Ammonia → 4-((3-Chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-ol

HRID 1879948Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

6-Acetoxy-4-(3-chloro-2-fluoroanilino)-7-methoxyquinazoline hydrochloride from step 1 (8.72 g, 21.9 mmol) was dissolved in methanol (200 ml). Concentrated aqueous ammonia (15 ml) was added, and the solution heated to 50° C. with stirring for 2 hours, causing precipitation of a cream coloured solid. The solid was collected by filtration, washed with diethyl ether (3×200 ml), and dried in vacuo at 60° C. over diphosphorous pentoxide, giving the product as an off white solid (5.40 g, 77%);

Workup

customprecipitation of a cream
filtrationThe solid was collected by filtration
washwashed with diethyl ether (3×200 ml)
dry with materialdried in vacuo at 60° C. over diphosphorous pentoxide

Sources & evidence

ORD record: ord-f4ec05411e80497aa812df8653d09488
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318752B2

Reaction notes

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