Water → 2-(Acetylamino)-5-(1-methylethyl)benzoic acid

HRID 1725867Notes

Reaction equation

HRID 1725867 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:14])[CH3:13].[OH2:15].CN(C)[CH:18]=[O:19]>C(N(CC)CC)C>[C:12]([NH:11][C:3]1[CH:4]=[CH:5][C:6]([CH:8]([CH3:10])[CH3:9])=[CH:7][C:2]=1[C:18]([OH:19])=[O:15])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 258023N-(2-Bromo-4-isopropylphenyl)acetamide

Product 1

HCID 127501112-(Acetylamino)-5-(1-methylethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of Example 2A (3.33 g, 13.0 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1.00 g, 1.2 mmol) in triethylamine (5.5 mL), dimethylformamide (25 mL), and water (5 mL) was shaken at 120° C. in a reactor pressurized with 850 psi of CO for 18 hours. The mixture was filtered, the filter cake was washed with ethyl acetate, and the combined filtrates were partitioned between diethyl ether and 1M NaOH. The aqueous phase was acidified with 12M HCl and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product (2.38 g). MS (ESI(+)) m/e 222 (M+H)+, 244 (M+Na)+; (ESI(−)) m/e 220 (M−H)−.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with ethyl acetate
  3. customthe combined filtrates were partitioned between diethyl ether and 1M NaOH
  4. extractionextracted twice with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-868ca0a9054c46449deae7dc35e0406b
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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