Anthranilic Acid → N-(2-Carboxyphenyl)phenoxyacetamide

HRID 1490301Notes

Reaction equation

HRID 1490301 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[O:11]([CH2:18][C:19](Cl)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>[OH-].[Na+]>[O:11]([CH2:18][C:19]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 69703Phenoxyacetyl chloride

Product 1

HCID 99325N-(2-Carboxyphenyl)phenoxyacetamideYield 81.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of anthranilic acid (5 g, 0.036 mol) in NaOH (3 g, 30 mL) was added phenoxyacetyl chloride (6.2 g, 5.2 mL) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 30 min, acidified with dilute hydrochloric acid and filtered. The filtered solid was dissolved in EtOAc and filtered. The filtrate was dried, filtered, concentrated and dried for 4 h under vacuum, affording 8 g (81%) of the title compound, mp 201°-203° C. A small amount (100 mg) of the title compound was recrystallized from EtOH, affording 75 mg of the title compound, mp 202°-203° C.; 1H NMR (DMSO-d6) δ 13.70 (s, 1H, COOH), 12.20 (s, 1H, NH), 8.71 (d, 1H, J=8.4), 8.02 (dd, 1H, J=7.6), 7.65-7.60 (m, 1H), 7.35-6.89 (m, 6H), 4.73 (s, 2H) ; 13C NMR (DMSO-d6) δ 169.44, 167.23, 157.11, 140.22, 134.34, 131.32, 129.65, 129.45, 123.06, 121.65, 120.96, 119.45, 116.14, 114.81, 114.38, 67.22; MS (EI, m/z) 271 (M+).

Workup

  1. filtrationfiltered
  2. dissolutionThe filtered solid was dissolved in EtOAc
  3. filtrationfiltered
  4. customThe filtrate was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried for 4 h under vacuum

Sources & evidence

ORD record
ord-1e50696dbdbd461b8bd75ab14a366ded
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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