Claims
- 1. A process for producing a benzamide derivative of the formula (A'): ##STR43## wherein R.sub.1 is hydrogen, and R' is C.sub.1 -C.sub.6 alkoxy, C.sub.6 cycloalkoxy, lower alkenylalkoxy and lower alkoxyalkoxy, which comprises reacting a compound of the formula (I): ##STR44## wherein R.sub.1 is as defined above with a suitable alcohol in the presence of a dehydrating-condensing agent, and wherein the compound of the formula (I) is prepared by reacting an acid amide derivative of the formula (III'): ##STR45## with sodium nitrite.
- 2. The process of claim 1, which is conducted in an organic solvent, and wherein said dehydrating-condensing agent is dicyclohexyl carbodiimide or N,N'-carbonyl diimidazole.
- 3. The process of claim 1, wherein said reaction of the acid amide derivative with sodium nitrite is effected in acetic acid in the presence of concentrated sulfuric acid.
- 4. The process of claim 1, wherein said suitable alcohol is selected from the group consisting of a suitable lower alkyl alcohol, lower alkenyl alcohol and a lower alkoxy alcohol.
- 5. A process for producing a benzamide derivative of the formula (A'): ##STR46## wherein R.sub.1 is hydrogen, and R' is C.sub.1 -C.sub.4 -monoalkylamino, mono-(lower)alkenylamino or di-(lower)alkylamino, which comprises reacting a compound of the formula (I): ##STR47## wherein R.sub.1 is as defined above, with a suitable amine in the presence of a dehydrating-condensing agent, and wherein the compound of the formula (I) is prepared by reacting an acid amide derivative of the formula (III'): ##STR48## with sodium nitrite.
- 6. The process of claim 5, wherein said suitable amine is selected from the group consisting of a suitable lower monoalkylamine, lower dialkylamine or lower alkenylamine.
- 7. The process of claim 5, which is conducted in an organic solvent, and wherein said dehydrating condensing agent is dicyclohexyl carbodiimide or N,N'-carbonyl diamidazole.
- 8. The process of claim 5, wherein said reaction of the acid amide derivative with sodium nitrite is effected in acetic acid in the presence of a sulfuric acid catalyst.
- 9. A process for producing a benzamide derivative of the formula (A'): ##STR49## wherein R.sub.1 is methyl, and R' is C.sub.1 -C.sub.6 alkoxy, C.sub.6 cycloalkoxy, lower alkenylalkoxy, which comprises:
- a) reacting a compound of the formula (I): ##STR50## wherein R.sub.1 is as defined above, with a suitable alcohol in the presence of a dehydrating-condensing agent, and wherein the compound of the formula (I) is prepared by reacting an acid chloride derivative of the formula (VI): ##STR51## with 2,3-dichloroaniline to obtain a compound of the formula (VII): ##STR52## and hydrolyzing the compound of the formula (VII).
- 10. The process of claim 9, wherein said suitable alcohol is selected from the group consisting of a lower alkyl alcohol, lower alkenyl alcohol and a lower alkoxy alcohol.
- 11. The process of claim 9, which is conducted in a organic solvent, and wherein said dehydrating-condensing agent is dicyclohexyl carbodiimide or N,N'-carbonyl diimidazole.
- 12. The process of claim 9, wherein said reaction of the compound of the formula (I) and said suitable alcohol is conducted in toluene in the presence of concentrated sulfuric acid.
- 13. The process of claim 9, wherein said acid chloride derivative is reacted with 2,3-dichloroaniline in an organic solvent in the presence of an acid acceptor to form the compound of the formula (VII).
- 14. The process of claim 13, wherein said solvent is acetone and said acid acceptor is sodium hydrogen carbonate.
- 15. The process of claim 13, wherein the compound of the formula (VIII) is hydrolyzed with sodium hydroxide to form the compound of the formula (I).
- 16. A process for producing a benzamide derivative of the formula (A'): ##STR53## wherein R.sub.1 is methyl, and R.sup.1 is C.sub.1 -C.sub.4 -monoalkylamino, mono-(lower) alkenylamino or di-(lower)alkylamino, which comprises:
- a) reacting a compound of the formula (I): ##STR54## wherein R.sub.1 is as defined above, with a suitable amine in the presence of a dehydrating-condensing agent, and wherein the compound of the formula (I) is prepared by reacting an acid chloride derivative of the formula (VI): ##STR55## with 2,3-dichloroaniline to obtain a compound of the formula (VII): ##STR56## and hydrolyzing the compound of the formula (VII).
- 17. The process of claim 16, wherein said suitable alcohol is selected from the group consisting of a suitable lower monoalkylamine, lower dialkylamine or lower alkenylamine.
- 18. The process of claim 16, which is conducted in a organic solvent, and wherein said dehydrating-condensing agent is dicyclohexyl carbodiimide or N,N'-carbonyl diimidazole.
- 19. The process of claim 16, wherein said reaction of the compound of the formula (I) and said suitable alcohol is conducted in toluene in the presence of concentrated sulfuric acid.
- 20. The process of claim 16, wherein said acid chloride derivative is reacted with 2,3-dichloroaniline in an organic solvent in the presence of an acid acceptor to form the compound of the formula (VII).
- 21. The process of claim 20, wherein said solvent is acetone and said acid acceptor is sodium hydrogen carbonate.
- 22. The process of claim 16, wherein the compound of the Formula (VII) is hydrolyzed with sodium hydroxide to form the compound of the formula (I).
Priority Claims (1)
Number |
Date |
Country |
Kind |
63-323568 |
Dec 1988 |
JPX |
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Parent Case Info
This is a division of Ser. No. 450,440, filed Dec. 14, 1989, now U.S. Pat. No. 5,043,006.
US Referenced Citations (8)
Foreign Referenced Citations (1)
Number |
Date |
Country |
733136 |
Apr 1966 |
CAX |
Non-Patent Literature Citations (4)
Entry |
Gutsche et al., Fundanentalc of Organic Chemistry, Prentice-Hall, Englewood Cliffs (1975). pp. 405, 841-851. |
The Merck Index, 11th ed., Merck & Co., Rahway (1989) p. 1365. |
Survey of Organic Synthesis, Calvin A. Buehler, University of Tennessee and Donald E. Pearson, Vanderbilt University, 1970. |
Organisch-Chemische Experimentierkunst, Prof. Dr. Phil. Habil. G. hilgetac, Inst. for Organic Chemistry, Berlin, 1964. |
Divisions (1)
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Number |
Date |
Country |
Parent |
450440 |
Dec 1989 |
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