Acetic Acid → 6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one

HRID 631206Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([OH:14])=[CH:8][C:3]=1[C:4](OC)=[O:5].CC(O)=O.O.[CH:20]([NH2:22])=O>>[OH:14][C:9]1[CH:8]=[C:3]2[C:2](=[CH:11][C:10]=1[O:12][CH3:13])[N:1]=[CH:20][NH:22][C:4]2=[O:5]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 713Formamide

HCID 962Water

HCID 23132492Methyl 2-amino-5-hydroxy-4-methoxybenzoate

Product 1

HCID 1354464136-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-oneYield 89%

Conditions

Temperature: 140 °C

Procedure

A mixture of methyl 2-amino-5-hydroxy-4-methoxybenzoate (3.1 g, 15.7 mmol) and AcOH (7.1 mL) in formamide (15.5 mL) was heated at 140° C. overnight. To it was added water (20 mL) and filtered to afford 6-hydroxy-7-methoxyquinazoline-4(3H)-one as a solid (2.7 g, 89%). 1H NMR (300 MHz, DMSO-d6) δ 9.82 (s, 1H), 7.9 (s, 1H), 7.4 (s, 1H), 7.1 (s, 1H), 3.9 (s, 3H).

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-216d8694bdf04a5b87ee05f530f602ef
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09320739B2

Reaction notes

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