Acetic Acid → HCID 68603399, compound

HRID 641958Notes

Reaction equation

HRID 641958 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:13](OC(OCC)OCC)C.C(O)(=O)C.[CH3:27][O:28][C:29](=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([NH2:37])[CH:31]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:12][O:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[CH:13][N:37]([C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][C:33]=1[CH3:36])[C:29]([O:28][CH3:27])=[O:38])[C:4]2=[O:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 2779305-Methoxyanthranilic acidHCID 337778Methyl 3-amino-4-methylbenzoate

Product 1

HCID 68603399HCID 68603399, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-amino-5-methoxybenzoic acid (18.7 g) in toluene (250 ml) was added triethylorthoformate (19.6 ml) and acetic acid (0.64 ml) and heated at 110° C. for 3 hours when methyl-3-amino-4-methylbenzoate (16.7 g) was added and heating continued for a further 16 hours at 110° C. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic phase was washed with 1N NaOH and 1N HCl. The organic phase was left to stand for 54 hours which resulted in crystallisation of a solid which was collected by filtration and air dried to give methyl 3-(6-methoxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate (9.3 g); NMR Spectrum: (DMSOd6) 2.18 (s, 3H), 3.84 (s, 3H), 3.92 (s, 3H), 7.28 (m, 1H), 7.59 (m, 2H), 7.73 (d, 1H), 7.93 (s, 1H), 7.98 (m, 1H), 8.19 (s, 1H); Mass Spectrum: M+H+ 325.

Workup

  1. additionwas added
  2. temperatureheating
  3. washThe organic phase was washed with 1N NaOH and 1N HCl
  4. waitThe organic phase was left
  5. waitto stand for 54 hours
  6. customwhich resulted in crystallisation of a solid which
  7. filtrationwas collected by filtration and air
  8. customdried

Sources & evidence

ORD record
ord-ee5450e6d13b41e8845147a28b74d5d1
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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