6-Methylanthranilic acid → 5-Methyl-4-quinazolone

HRID 1058859Notes

Reaction equation

HRID 1058859 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8](O)=[O:9].C(O)(=O)C.[CH:16](N)=[NH:17]>C(OCCO)C>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[C:8](=[O:9])[NH:17][CH:16]=[N:11]2

Participants

4

Reactant 2

HCID 1512106-Methylanthranilic acidHCID 160693Formamidine acetate

Product 1

HCID 1354187585-Methyl-4-quinazoloneYield 68.1%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

6-Methylanthranilic acid (5 g, 33 mmol) and formamidine acetate (0.4 g, 41 mmol) were refluxed in 2-ethyoxyethanol (50 ml) for 16 h. On cooling the solvent was removed in vacuo, the residue slurried in diethyl ether, the solid filtered, washed with diethyl ether and dried to yield 3.6 g of the title compound. δH (DMSO d6), 7.97 (1H, s), 7.60 (1H, dd, J 7.9, 7.6 Hz), 7.43 (1H, d, J 8.0 Hz), 7.21 (1H, d, J 7.3 Hz), 2.76 (3H, s); m/z (ES+70V)161 (MH+).

Workup

  1. temperatureOn cooling the solvent
  2. customwas removed in vacuo
  3. filtrationthe solid filtered
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-a6b3395974d04978aadd466140c70fad
Source dataset
uspto-grants-2003_02
Patent number
US06518283B1

Reaction notes

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