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

HRID 600928Notes

Reaction equation

HRID 600928 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-339cb83e618543e7a4d698ed37b8a218
Source dataset
uspto-grants-2011_03
Patent number
US07902241B2

Reaction notes

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