Acetic Acid → 2-(3-chlorophenyl)-6-hydroxy-3-methylquinazolin-4(3H)-one

HRID 77398Notes

Reaction equation

HRID 77398 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)C=O.[C:22](O)(=O)C>C(O)C.[O-2].[Mn+4].[O-2]>[Cl:13][C:14]1[CH:21]=[C:20]([C:7]2[N:6]([CH3:22])[C:4](=[O:5])[C:3]3[C:2](=[CH:11][CH:10]=[C:9]([OH:12])[CH:8]=3)[N:1]=2)[CH:19]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 114773-ChlorobenzaldehydeHCID 699296892-amino-5-hydroxy-N-methylbenzamide2×

Product 1

HCID 699287212-(3-chlorophenyl)-6-hydroxy-3-methylquinazolin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-amino-5-hydroxy-N-methylbenzamide (Intermediate 32A) (280 mg, 1.68 mmol) and 3-chlorobenzaldehyde (0.23 mL, 2.02 mmol) in ethanol (10 mL) was added a catalytic amount of acetic acid (0.07 mL) and the mixture heated under reflux for 23 h. The reaction was cooled before manganese (iv) oxide (225 mg, 1.68 mmol) was added and the reaction heated under reflux until complete by Ic/ms. On cooling the reaction was filtered and the filtrate evaporated to dryness to afford 2-(3-chlorophenyl)-6-hydroxy-3-methylquinazolin-4(3H)-one (450 mg, 1.57 mmol).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 23 h
  3. additionwas added
  4. temperaturethe reaction heated
  5. temperatureunder reflux until complete by Ic/ms
  6. temperatureOn cooling the reaction
  7. filtrationwas filtered
  8. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-2011fbcdf67e4f5f91155dc6d8643c93
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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