4-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)7-nitroquinazoline hydrochloride → 7-Amino4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochloride
Reaction equation
[ClH:1].[F:2][C:3]1[CH:22]=[C:21]([CH3:23])[C:20]([O:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][C:4]=1[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-])=O)=[CH:13][CH:14]=2)[N:9]=[CH:8][N:7]=1>[Pd].C(O)C.Cl.CO>[ClH:1].[NH2:16][C:12]1[CH:11]=[C:10]2[C:15]([C:6]([NH:5][C:4]3[CH:19]=[C:20]([O:24][C:25]([O:27][CH3:28])=[O:26])[C:21]([CH3:23])=[CH:22][C:3]=3[F:2])=[N:7][CH:8]=[N:9]2)=[CH:14][CH:13]=1Participants
6
Reactant 1
Product 1
Reagents, catalysts & solvents 4
Procedure
A mixture of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-nitroquinazoline hydrochloride (5.3 g, 13 mmol) and 10% palladium-on-charcoal catalyst (1 g) in ethanol (100 ml), 7M ethanolic hydrogen chloride (1.8 ml) and methanol (20 ml) was stirred under hydrogen at 1.7 atmospheres for 75 minutes. The catalyst was removed by filtration through diatomaceous earth and the filter pad thoroughly washed with methylene chloride, methanol and ether and the solvent was removed from the filtrate by evaporation to give 7-amino-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochloride (4.8 g, 97%) as a yellow solid.
Workup
- customThe catalyst was removed by filtration through diatomaceous earth
- washthe filter pad thoroughly washed with methylene chloride, methanol and ether
- customthe solvent was removed from the filtrate by evaporation
Sources & evidence
- ORD record
- ord-f6b0a6199cb3477297a967c0069218d2
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06184225B2
Reaction notes
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