Water → HCID 709184, compound

HRID 238213Notes

Reaction equation

HRID 238213 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(=[O:16])[CH:13]([CH3:15])[CH3:14].O>CN(C=O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 124762-Amino-5-chlorobenzoic acidHCID 62325Isobutyryl chloride

Product 1

HCID 709184HCID 709184, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-chloro-benzoic acid (3.43 g, 20 mmol) in DMF (10 mL) cooled in an ice-water bath was added isobutyryl chloride (2.11 mL, 20 mmol). The reaction was stirred for 2 hours while warming to room temperature. Water (20 mL) was added and the mixture was stirred vigorously for 1 hour. The precipitate was then collected by vacuum filtration to give the product as a pale yellow solid (3.20 g, 66%). 1H NMR (400 MHz, DMSO-d6) δ 11.13 (s, 1H), 8.52 (d, J=9.0 Hz, 1H), 7.92 (d, J=2.6 Hz, 1H), 7.66 (dd, J=9.0, 2.7 Hz, 1H), 2.58 (septet, J=6.9 Hz, 1H), 1.16 (d, J=6.9 Hz, 6H).

Workup

  1. stirringthe mixture was stirred vigorously for 1 hour
  2. filtrationThe precipitate was then collected by vacuum filtration

Sources & evidence

ORD record
ord-7697102fe81845d58a92d0ec3dd3a38c
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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