4,5-Dimethoxyanthranilic acid → 6,7-Dimethoxy-3H-quinazolin-4-one

HRID 1929783Notes

Reaction equation

HRID 1929783 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:14])[C:6](=[CH:10][C:11]=1[O:12][CH3:13])[C:7](O)=[O:8].Cl.[CH:16](N)=[NH:17]>[OH-].[Na+]>[CH3:13][O:12][C:11]1[CH:10]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[N:14]=[CH:16][NH:17][C:7]2=[O:8]

Participants

4

Reactant 2

HCID 797364,5-Dimethoxyanthranilic acidHCID 10313058Methanimidamide, hydrochloride (1:1)

Product 1

HCID 1354950166,7-Dimethoxy-3H-quinazolin-4-oneYield 64%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
210 °C

Procedure

36.9 g of 4,5-dimethoxyanthranilic acid was mixed with 25.0 g of formamidine hydrochloride, and the mixture was stirred at 210° C. for 30 minutes. After completion of the reaction, the solid thus obtained was cooled to room temperature, stirred with 200 ml (0.33 M) of aqueous sodium hydroxide and filtered under a reduced pressure. The solid thus obtained was washed with water and air-dried to obtain the title compound (24.6 g, 64%).

Workup

  1. customAfter completion of the reaction
  2. customthe solid thus obtained
  3. temperaturewas cooled to room temperature
  4. filtrationfiltered under a reduced pressure
  5. customThe solid thus obtained
  6. washwas washed with water
  7. customair-dried

Sources & evidence

ORD record
ord-a0e63b5519374124ac5c5f1ed5ba2488
Source dataset
uspto-grants-2012_05
Patent number
US08188102B2

Reaction notes

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