Methanol → 7-Amino4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochloride

HRID 1384662Notes

Reaction equation

HRID 1384662 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.CO>[Pd].C(O)C.Cl>[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]=1

Participants

6

Reactant 2

HCID 887MethanolHCID 226250474-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)7-nitroquinazoline hydrochloride

Product 1

HCID 226250847-Amino4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochlorideYield 97.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

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 (10 ml), ethanolic hydrogen chloride (1.8 ml of a 7M solution) and methanol (20 ml) was stirred under hydrogen at 1.7 atmospheres pressure 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. 1H NMR Spectrum: (DMSOd6) 2.22(s, 3H); 3.87(s, 3H); 6.77(s, 1H); 7.08(dd, 1H); 7.15(m, 2H); 7.41(m, 2H); 8.35(d, 1H); 8.63(s, 1H); 11.03(s, 1H) MS-ESI: 343 [MH]+

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washthe filter pad thoroughly washed with methylene chloride, methanol and ether
  3. customthe solvent was removed from the filtrate by evaporation

Sources & evidence

ORD record
ord-d22b95a0743b43309933ff00cbede098
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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