4-Methyl-3-nitroaniline → HCID 22732279, compound

HRID 1357684Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]>>[ClH:1].[CH3:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]

Participants

Reactant 2

HCID 83904-Methyl-3-nitroaniline

HCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 22732279HCID 22732279, compound

Procedure

Using analogous procedures to those described in the portion of Example 2 which is concerned with the preparation of starting materials, 4-chloro-6,7-dimethoxyquinazoline was reacted with 4-methyl-3-nitroaniline to give 4-(4-methyl-3-nitroanilino)-6,7-dimethoxyquinazoline hydrochloride; NMR: 2.54 (s, 3H), 3.98 (s, 3H), 4.02 (s, 3H), 7.38 (s, 1H), 7.58 (m, 1H), 8.06 (m, 1H), 8.43 (m, 2H), 8.89 (s, 1H), 11.72 (s, 1H); Mass: M+H+ 341 and that material was reduced during 5 hours to give 4-(3-amino-4-methylanilino)-6,7-dimethoxyquinazoline; NMR: 2.04 (s, 3H), 3.9 (s, 3H), 3.92 (s, 3H), 4.88 (s, 2H), 6.8 (m, 1H), 6.9 (m, 1H), 7.03 (s, 1H), 7.12 (m, 1H), 7.8 (s, 1H), 8.38 (s, 1H); 9.2 (s, 1H); Mass: M+H+ 311.

Sources & evidence

ORD record: ord-fe621de2a7ab49a687f0063553f7892f
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06593333B1

Reaction notes

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