Methyl 3-amino-4-methylbenzoate → HCID 58861396, compound

HRID 1350798Notes

Reaction equation

HRID 1350798 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]=1[CH2:10][CH3:11])=[O:4].[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([NH2:28])[CH:22]=1>CCO>[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([NH:28][CH2:2][C:3]([C:5]2[CH:6]=[N:7][N:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]=2[CH2:10][CH3:11])=[O:4])[CH:22]=1

Participants

4

Reactant 2

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 21097268HCID 21097268, compound

Product 1

HCID 58861396HCID 58861396, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7.20 g (24.6 mmol) of 2-bromo-1-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-ethanone and 8.52 g (51.6 mmol) of 3-amino-4-methyl benzoic acid methyl ester in EtOH (30 mL) was heated to 75° C. for 16 h. The solution was cooled and allowed to stand at rt for 6 h. The solids were filtered off and washed with cold EtOH to provide 3-[2-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethylamino]-4-methyl-benzoic acid methyl ester as a white powder (3.75 g). ESI MS m/z 378 [C22H23N3O3+H]+.

Workup

  1. temperatureThe solution was cooled
  2. filtrationThe solids were filtered off
  3. washwashed with cold EtOH

Sources & evidence

ORD record
ord-7c357e4c8d9247ecb0e10dba643613d9
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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