6-(benzyloxy)-7-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one → HCID 136078808, compound

HRID 1406995Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[C:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1)[NH:13][C:12]2=[O:30])C1C=CC=CC=1>FC(F)(F)C(O)=O>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[C:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1)[NH:13][C:12]2=[O:30]

Participants

Conditions

Temperature: 75 °C

Procedure

To a suspension of 6-(benzyloxy)-7-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (3.21 g, 7.95 mmol) in trifluoroacetic acid (45 mL) was heated at 75±5° C. for 2.5 h. The volatiles were removed in vacuo and residue was taken up with sat. NaHCO3 solution. A light yellow colored solid separated out, which was collected via filtration. The solid was washed with water and dried under vacuum to give 6-hydroxy-7-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (2.38 g, 7.60 mmol, 96%). HPLC retention time 5.486 min.

Workup

customThe volatiles were removed in vacuo and residue
customA light yellow colored solid separated out
filtrationwhich was collected via filtration
washThe solid was washed with water
customdried under vacuum

Sources & evidence

ORD record: ord-99044701b2784dce8e196e0f2dfe9389
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916576B2

Reaction notes

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