Dimethylformamide → 3-[2-(3-Isopropylphenylamino)acetylamino]benzoic acid methyl ester

HRID 2194826Notes

Reaction equation

HRID 2194826 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:14])[CH2:12]Br)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH:22]([C:25]1[CH:31]=[CH:30][C:28](N)=[CH:27][CH:26]=1)([CH3:24])[CH3:23].C[N:33](C=O)C>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:14])[CH2:12][NH:33][C:27]2[CH:28]=[CH:30][CH:31]=[C:25]([CH:22]([CH3:24])[CH3:23])[CH:26]=2)[CH:5]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 74644-IsopropylanilineHCID 11430Potassium CarbonateHCID 20317589Methyl 3-(2-bromoacetamido)benzoate

Product 1

HCID 666031253-[2-(3-Isopropylphenylamino)acetylamino]benzoic acid methyl esterYield 84.5%

Procedure

3-(2-Bromoacetylamino)benzoic acid methyl ester (8.09 g, 29.7 mmol) prepare above was mixed with potassium carbonate (4.93 g, 35.7 mmol) and 4-isopropylaniline (4.41 g, 32.7 mmol) in DMF (100 mL), and the mixture was stirred at room temperature overnight. The solvent was then removed in vacuum and the residue was suspended in dichloromethane. The solid was filtered off and the filtrate was concentrated to give crude product, which was chromatographed (silica gel, hexanes:ethyl acetate, 8:2) to give 3-[2-(3-isopropylphenylamino)acetylamino]benzoic acid methyl ester as a pale yellow oil (8.18 g, 84.5%). MS (ES+) m/z: 327.

Workup

  1. customThe solvent was then removed in vacuum
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated
  4. customto give crude product, which
  5. customwas chromatographed (silica gel, hexanes:ethyl acetate, 8:2)

Sources & evidence

ORD record
ord-be7cb7c5f8164d7792965e333bd0e302
Source dataset
uspto-grants-2012_12
Patent number
US08334313B2

Reaction notes

Loading…