Methyl 4-Formylbenzoate → HCID 136947746, compound

HRID 1050961Notes

Reaction equation

HRID 1050961 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:13]([C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)=O.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>CN1CCCC1=O>[CH3:22][O:21][C:19](=[O:20])[C:18]1[CH:23]=[CH:24][C:15]([C:13]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[C:10]([F:11])[CH:9]=[C:8]([F:12])[CH:7]=3)[N:1]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 24346Disodium disulfiteHCID 67358340HCID 67358340, compound

Product 1

HCID 136947746HCID 136947746, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-amino-3,5-difluoro-benzamide (86.2 mg, 0.50 mmol), methyl 4-formylbenzoate (82.1 mg, 0.50 mmol) and sodium disulfite (97 mg, 0.51 mmol) in N-methyl-pyrrolidone (1 ml) is heated to 150° C. and stirred at this temperature for 16 hours. The reaction mixture is allowed to reach room temperature and poured into ice water. The resulting precipitate is collected by filtration, washed with water and dried under vacuum to afford 4-(6,8-difluoro-4-oxo-3,4-dihydro-quinazolin-2-yl)-benzoic acid methyl ester as brown solid; HPLC/MS 1.88 min (A), [M+H] 316.

Workup

  1. customto reach room temperature
  2. filtrationThe resulting precipitate is collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-096fe315a1a54933a29318a5d89dc35c
Source dataset
uspto-grants-2016_07
Patent number
US09388142B2

Reaction notes

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