Anthranilic Acid → 2-Propanamidobenzoic acid

HRID 238192Notes

Reaction equation

HRID 238192 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11](Cl)(=[O:14])[CH2:12][CH3:13].O>CN(C=O)C>[C:11]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])(=[O:14])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 962WaterHCID 62324Propionyl chloride

Product 1

HCID 32646742-Propanamidobenzoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of anthranilic acid (2.96 g, 21.6 mmol) in DMF (10 mL) cooled in an ice-water bath was added propionyl chloride. 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 white solid (3.11 g, 75%). 1H NMR (CDCl3) δ 1.32 (t, 3H, J=7.6 Hz), 2.53 (q, 2H, J=7.6 Hz), 7.14 (t, 1H, J=8.2 Hz), 7.62 (t, 1H, J=8.7 Hz), 8.15 (dd, 1H, J=1.5, 8.1 Hz), 8.79 (dd, 1H, J=0.9, 8.5 Hz), 10.97 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-7c703ab852c04434ae5f61e4fc54ee6b
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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