Claims
- 1. A process to produce a compound of the formula ##STR94## wherein A is ##STR95## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, alkoxy lower alkyl, halo lower alkyl; R is hydrogen or lower alkyl; R.sub.3 is selected from the group consisting of hydrogen and lower akyl; R.sub.4 is selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, lower alkyl, mono- or di-C.sub.1 to C.sub.7 alkyl or phenyl, chlorophenyl or tolyl substituted amino, amino, hydroxy lower alkyl and lower alkanoyl; R.sub.6 is selected from the group consisting of phenyl, mono-halo or mono-nitro substituted phenyl, di-halo or halo-nitro substituted phenyl, pyridyl and mono-halo or mono-nitro substituted pyridyl; and ##STR96## is selected from the group consisting of ##STR97## which comprises the stepwise reaction of a compound of the formula ##STR98## wherein R.sub.3, R.sub.4, R.sub.6, A and ##STR99## are as above and the leaving group is selected from the group consisting of alkoxides, alkylthio, halo, cyano, phosphate and nitrosoalkylamino
- (a) with the anion generated from malonic ester, i.e., a compound of the formula ##STR100## wherein R is lower alkyl; (b) decarboxylating with an alkali metal hydroxide the product of (a);
- (c) nitrosating with nitrous acid the product of (b);
- (d) reducing with H.sub.2 /Raney nickel or zinc/acetic acid the product of (c);
- (e) reacting the product of (d) with an alkanoic acid ortho ester of the formula
- R.sub.1 C(OR).sub.3
- wherein R is lower alkyl and R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, alkoxy lower alkyl, halo lower alkyl, to produce the final product as an ester, i.e., R=lower alkyl;
- (f) if desired, hydrolysing with alkali metal hydroxides the product of (e) to the final product as as acid, i.e., R=hydrogen.
Parent Case Info
This is a division of application Ser. No. 905,820 filed May 15, 1978, now U.S. Pat. No. 4,280,957 which is a continuation of Ser. No. 663,660, filed Mar. 4, 1978 (now abandoned) which is a CIP of Ser. No. 602,691, filed Aug. 7, 1975 (now abandoned) which is a CIP of Ser. No. 504,924, filed Sept. 11, 1974 (now abandoned).
US Referenced Citations (7)
Non-Patent Literature Citations (1)
Entry |
Fryer, et al., J. Heterocyclic Chemistry, vol. 15, pp. 619-624 (6/78). |
Divisions (1)
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Number |
Date |
Country |
Parent |
905820 |
May 1978 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
663660 |
Mar 1978 |
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
602691 |
Aug 1975 |
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Parent |
504924 |
Sep 1974 |
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