Acetic Anhydride → 6-Acetoxy-7-methoxy-3H-quinazolin-4-one

HRID 712374Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[CH:7][NH:6][C:5]2=[O:14].[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[C:15]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[CH:7][NH:6][C:5]2=[O:14])(=[O:17])[CH3:16]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 6-hydroxy-7-methoxyquinazolin-4(3H)-one (0.57 g) and pyridine (4 mL) was added acetic anhydride (10 mL) at room temperature. The reaction mixture was stirred at 100° C. for 3 hours, and then poured into ice-water. The resulting mixture was filtered to give the title compound (0.40 g, 53.00%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, d6-DMSO) δ: 2.30 (s, 3H), 3.92 (s, 3H), 7.28 (s, 1H), 7.75 (s, 1H), 8.08 (s, 1H).

Workup

filtrationThe resulting mixture was filtered

Sources & evidence

ORD record: ord-3545deae1bab4dfd8f60772329e94d1d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181277B2

Reaction notes

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