Claims
- 1. A process for producing quinazoline derivatives represented by the formula, ##STR7## wherein R.sub.1 and R.sub.2 are individually a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a nitro group, a trifluoromethyl group, a C.sub.1 - C.sub.4 alkylthio group, a C.sub.1-C.sub.4 alkylsulfonyl group or a halogen atom; R.sub.3 is a phenyl group, a halophenyl group, a C.sub.1 -C.sub.4 alkylphenyl group, a C.sub.1 - C.sub.4 alkoxyphenyl group, a trifluoromethylphenyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.5 -C.sub.6 cycloalkenyl group, a pyridyl group, a furyl group, a thienyl group or a naphthyl group; and R is a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.4 alkenyl group, a C.sub.1 -C.sub.4 haloalkyl group, a benzyl, phenethyl, chlorobenzyl or fluorobenzyl group, a C.sub.3 - C.sub.6 cycloalkyl group, a C.sub.3 -C.sub.6 cycloalkyl C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 hydroxyalkyl group, a C.sub.1 -C.sub.4 alkanoyloxy C.sub.1 -C.sub.4 alkyl group, a trihalomethyl C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkylthioalkyl group or a group of the formula ##STR8## (wherein n is an integer of 1 to 3; R.sub.4 and R.sub.5 are individually a C.sub.1 -C.sub.4 alkyl group provided that R.sub.4 and R.sub.5 may form together with the adjacent nitrogen atom an unsubstituted or optionally substituted 5-or 6-membered heterocyclic ring, which may further contain a hetero atom), which comprises contacting a 2-aminophenyl ketone derivative represented by the formula, ##STR9## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above, with an alkali metal hydride to form a metal salt of 2-aminophenyl ketone derivative represented by the formula, ##STR10## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above; and M is an alkali metal atom, thereafter reacting the resultant metal salt of the formula (III) with a compound of the formula RX where R is as defined above and X is halogen to prepare a 2-(N-mono-substituted amino) phenyl ketone derivative represented by the formula, ##STR11## wherein R.sub.1, R.sub.2, R.sub.3 and R are as defined above, and then, reacting the compound of the formula (V) with a lower alkyl haloformate or a benzyl haloformate to yield a carbamate derivative represented by the formula, ##STR12## wherein R.sub.1, R.sub.2, R.sub.3 and R are as defined above; and R.sub.6 is a C.sub.1 -C.sub.4 alkyl group or a benzyl group, and finally reacting the compound of the formula (VI) with ammonia.
- 2. A process for producing 2-(N-mono-substituted amino)-phenyl ketone derivatives represented by the formula, ##STR13## wherein R.sub.1, R.sub.2, R.sub.3 and R are as defined in claim 1, which comprises contacting a 2-aminophenyl ketone derivative represented by the formula, ##STR14## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined in claim 1, with an alkali metal hydride to form a metal salt of 2-aminophenyl ketone derivative represented by the formula, ##STR15## wherein R.sub.1, R.sub.2, R.sub.3 and M are as defined in claim 1, and reacting the resultant metal salt of the formula (III) with a compound of the formula RX where R is as defined above and X is halogen.
- 3. A process according to claim 2, wherein the compound of the formula (V), is prepared by reacting the metal salt (III) with the compound of the formula RX in a solvent.
- 4. A process according to claim 2, wherein the alkali metal hydride is sodium hydride or potassium hydride.
- 5. A process according to claim 3, wherein the solvent is selected from the group consisting of benzene, toluene, xylene, monochlorobenzene, dimethylacetamide, diethylacetamide, dimethylformamide, dioxane, dimethylsulfoxide and a mixture thereof.
- 6. A process for producing 2-(N-mono-substituted)-phenyl ketone derivatives represented by the formula, ##STR16## wherein R.sub.1 and R.sub.2 are individually a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a nitro group, a trifluoromethyl group, a C.sub.1 -C.sub.4 alkylthio group, a C.sub.1 -C.sub.4 alkylsulfonyl group or a halogen atom; R.sub.3 is a phenyl group, a halophenyl group, a C.sub.1 -C.sub.4 alkylphenyl group, a C.sub.1 -C.sub.4 alkoxyphenyl group, a trifluoromethylphenyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.5 -C.sub.6 cycloalkenyl group, or a naphthyl group; and R is a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.4 alkenyl group, a benzyl, phenethyl, chlorobenzyl or fluorobenzyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.3 -C.sub.6 cycloalkyl C.sub.1 -C.sub.4 alkyl group, or a trihalomethyl C.sub.1 -C.sub.4 alkyl group which comprises contacting a 2-aminophenyl ketone derivative represented by the formula, ##STR17## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above, with one equivalent or some excess amount of sodium hydride in dimethylformamide to form a sodium salt of 2-amino-phenyl ketone derivative represented by the formula, ##STR18## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above; and M is a sodium atom, thereafter reacting the resultant metal salt of the formula (III) with one equivalent or some excess amount of a compound of the formula RX where R is as defined above and X is halogen in dimethylformamide at room temperature.
- 7. A process according to claim 6 for producing 2-ethylamino-5-chlorobenzylphenone, wherein the compound of the formula RX is ethyl iodide, R.sub.1 is hydrogen, R.sub.2 is chlorine and R.sub.3 is a phenyl group.
- 8. A process according to claim 1, wherein X is chlorine, bromine or iodine.
- 9. A process according to claim 6, wherein X is chlorine, bromine or iodine.
Priority Claims (1)
Number |
Date |
Country |
Kind |
45-109975 |
Dec 1970 |
JA |
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Parent Case Info
This is a Continuation of application Ser. No. 203,049 filed Nov. 29, 1971, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
2809994 |
Hinckley |
Oct 1957 |
|
3109843 |
Reeder et al. |
Nov 1963 |
|
Non-Patent Literature Citations (1)
Entry |
Ott et al., "Chemical Abstracts," vol. 71, p. 302, 30502y (1969). |
Continuations (1)
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Number |
Date |
Country |
Parent |
203049 |
Nov 1971 |
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