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

HRID 1808507Notes

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-d01f5832e58242a5b6e4e275ecb0365f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357693B2

Reaction notes

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