Hydrochloric Acid → 4-(5-Fluorooxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline

HRID 1386266Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OCC)OCC)[C:6](=[O:18])[CH:5]2[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1.Cl>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:18])[CH:5]2[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-(5-fluoro-1-diethoxymethyloxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline (255 mg, 0.52 mmol), (prepared as described in Example 9), in ethanol (25 ml) containing 2M hydrochloric acid (2.6 ml) was heated at 80° C. for 1 hour. The solid formed was collected by filtration, washed with ethanol and dried under vacuum. The solid was dissolved in hot DMF, the solution was diluted with ethyl acetate and thoroughly washed with water. The organic layer was dried (MgSO4), the volatiles removed by evaporation and the resulting solid was dried under vacuum at 70° C. to give 4-(5-fluorooxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline (49 mg, 25%).

Workup

customThe solid formed
filtrationwas collected by filtration
washwashed with ethanol
customdried under vacuum
dissolutionThe solid was dissolved in hot DMF
additionthe solution was diluted with ethyl acetate
washthoroughly washed with water
dry with materialThe organic layer was dried (MgSO4)
customthe volatiles removed by evaporation
customthe resulting solid was dried under vacuum at 70° C.

Sources & evidence

ORD record: ord-0fc19aa321b747c6a1ed4839af81fa58
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265411B1

Reaction notes

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