3,4-Dimethoxyaniline → (3,4-Dimethoxy-phenyl)-(2-methyl-6-nitro-quinazolin-4-yl)-amine

HRID 1668799Notes

Reaction equation

HRID 1668799 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[C:4]([CH3:15])[N:3]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[NH2:21].C([O-])(=O)C.[Na+]>>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[C:4]([CH3:15])[N:3]=2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

4

Reactant 3

HCID 227703,4-DimethoxyanilineHCID 517045Sodium AcetateHCID 249038664-Chloro-2-methyl-6-nitroquinazoline

Product 1

HCID 59648372(3,4-Dimethoxy-phenyl)-(2-methyl-6-nitro-quinazolin-4-yl)-amine

Procedure

The title compound was prepared from 4-chloro-2-methyl-6-nitro-quinazoline (80 mg, 0.36 mmol), 3,4-dimethoxy-aniline (54.8 mg, 0.36 mmol) and sodium acetate (35.2 mg, 0.43 mmol) similar to example 20 to give 109 mg (89.5%) of yellow solids. 1H NMR (CDCl3): 8.87 (d, J=2.7 Hz, 1H), 8.56 (dd, J=2.4 Hz, J=9.0 Hz, 1H), 7.91 (d, J=9.0 Hz, 1H), 7.63-7.61 (m, 2H), 7.28-7.24 (m, 1H), 6.94 (d, J=8.7 Hz, 1H), 3.96 (s, 3H)), 3.93 (s, 3H), 2.71 (s, 3H).

Sources & evidence

ORD record
ord-c94ef82d12c54caa895638bc1abecdae
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

Loading…