5-Amino-4-fluoro-2-methylphenyl Methoxyformate → 4-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)7-nitroquinazoline hydrochloride

HRID 1421042Notes

Reaction equation

Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[N:6]=[CH:5][N:4]=1.[F:16][C:17]1[CH:23]=[C:22]([CH3:24])[C:21]([O:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20][C:18]=1[NH2:19]>C(O)(C)C>[ClH:2].[F:16][C:17]1[CH:23]=[C:22]([CH3:24])[C:21]([O:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20][C:18]=1[NH:19][C:3]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-chloro-7-nitroquinazoline hydrochloride (2.46 g, 10 mmol) and 2-fluoro-5-methoxycarbonyloxy-4-methylaniline (2.2 g, 1 mmol), (prepared as described for the starting material in Example 12), in isopropanol (25 ml) was heated at 50° C. for 1 hour. The mixture was allowed to cool, the precipitated solid was collected by filtration recrystallised from methylene chloride/methanol/isopropanol to give 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-nitroquinazoline hydrochloride (1.8 g, 45%) as a yellow solid.

Workup

temperatureto cool
filtrationthe precipitated solid was collected by filtration
customrecrystallised from methylene chloride/methanol/isopropanol

Sources & evidence

ORD record: ord-568f62166743424aa6153e915dd32268
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071921

Reaction notes

Loading…