Acetic Acid → HCID 178486822, compound

HRID 445523Notes

Reaction equation

HRID 445523 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[NH:14][C:15](=O)[CH3:16].C([O-])(=O)C.[NH4+:23].C(O)(=O)C>O>[CH3:11][O:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][C:7]=1[O:12][CH3:13])[N:14]=[C:15]([CH3:16])[N:23]=[C:3]2[OH:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 717609Methyl 2-acetamido-4,5-dimethoxybenzoate

Product 1

HCID 178486822HCID 178486822, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the crude 2-acetylamino-4,5-dimethoxy-benzoic acid methyl ester obtained above was added ammonium acetate (7.98 g, 0.104 mol) and acetic acid (10 mL). The mixture was heated at reflux in a pressure tube until the formation of the desired cyclization product, as indicated by LC/MS: m/z 221 (M+H). After cooling to RT, the reaction mixture was diluted with water, and extracted with EtOAc 3 times. The combined organic phase was basified with aq. NaOH solution, and washed 3 times with EtOAc. The aqueous layer was then acidified with aq. HCl and extracted three times with EtOAc. The combined organic extract was dired over Na2SO4 and concentrated in vacuo, affording 6,7-dimethoxy-2-methyl-quinazolin-4-ol (0.15 g), which was used without further purification. LC/MS: m/z 221 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux in a pressure tube until the formation of the desired cyclization product
  3. extractionextracted with EtOAc 3 times
  4. washwashed 3 times with EtOAc
  5. extractionextracted three times with EtOAc
  6. extractionThe combined organic extract
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ee8e9feaded4a90805968f88298f3ff
Source dataset
uspto-grants-2013_07
Patent number
US08476298B2

Reaction notes

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