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

HRID 61645Notes

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-6cda9b53b3d14ecdbd7c5c5a38475c6c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440961B2

Reaction notes

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