Formamide → 6,7-Dimethoxy-3H-quinazolin-4-one

HRID 2218934Notes

Reaction equation

HRID 2218934 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4](O)=[O:5].[CH:15]([NH2:17])=O>>[CH3:14][O:13][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[O:11][CH3:12])[N:1]=[CH:15][NH:17][C:4]2=[O:5]

Participants

3

Reactant 2

HCID 713FormamideHCID 797364,5-Dimethoxyanthranilic acid

Product 1

HCID 1354950166,7-Dimethoxy-3H-quinazolin-4-one

Conditions

Temperature
190 °C

Procedure

A mixture of 2-amino-4,5-dimethoxybenzoic acid (9.9 mg, 0.050 mmol) and formamide (5 ml) was heated at 190° C. for 6 hours. The mixture was cooled to 80° C. and poured onto water (25 ml). Precipitated material was filtered off, washed with water and dried in vacuo. Yield 1.54 g (15%), brown powder. The structure was confirmed by 1H (500 MHz) and 13C NMR (125 MHz) analysis.

Workup

  1. temperatureThe mixture was cooled to 80° C.
  2. additionpoured onto water (25 ml)
  3. filtrationPrecipitated material was filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bff766c77a0b4da18fdd9a010bdbcc89
Source dataset
uspto-grants-2008_08
Patent number
US07413727B2

Reaction notes

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