Methyl 4-Formylbenzoate → HCID 136947752, compound

HRID 1050956Notes

Reaction equation

HRID 1050956 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:12]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)=O.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>CN(C)C(=O)C>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([C:12]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][CH:9]=[C:8]([F:11])[CH:7]=3)[N:1]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 24346Disodium disulfiteHCID 102410032-Amino-5-fluorobenzamide

Product 1

HCID 136947752HCID 136947752, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 2-amino-5-fluorobenzamide (1.00 g, 6.49 mmol), methyl 4-formylbenzoate (1.06 g, 6.49 mmol) and sodium disulfite (1.26 g, 6.62 mmol) in N,N-dimethylacetamide (13 ml) is heated to 150° C. and stirred at this temperature for 3 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-fluoro-4-oxo-3,4-dihydro-quinazolin-2-yl)-benzoic acid methyl ester as yellow solid; HPLC/MS 2.08 min (C), [M+H] 299.

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-6ac11753432b4d20a9c2c8dcaa8b5a26
Source dataset
uspto-grants-2016_07
Patent number
US09388142B2

Reaction notes

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