Hydrochloric Acid → 3-methyl-N-(2-methylphenoxyacetyl)anthranilic acid

HRID 1587421Notes

Reaction equation

HRID 1587421 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].[CH3:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[O:15][CH2:16][C:17](Cl)=[O:18].Cl>[OH-].[Na+]>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH:11][C:17](=[O:18])[CH2:16][O:15][C:14]1[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=1[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 781012-Amino-3-methylbenzoic acidHCID 12353488(2-Methylphenoxy)acetyl chloride

Product 1

HCID 197577613-methyl-N-(2-methylphenoxyacetyl)anthranilic acidYield 94.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3-Methylanthranilic acid 1.0 g (6 mmol) was dissolved in 10% aqueous sodium hydroxide solution 27 ml and to this soulution, 2-methylphenoxyacetyl chloride 1.3 g (7.3 mmol) was added dropwise at 0° C. The resulting solution was stirred at room temperature for 5 minutes and acidified with 10% hydrochloric acid solution. Deposited crystals were collected by filtration, washed with hot water and recrystallized from ethanol to obtain 3-methyl-N-(2-methylphenoxyacetyl)anthranilic acid (melting point: 133° to 136° C.) 1.7 g (yield: 83%).

Workup

  1. additionwas added dropwise at 0° C
  2. filtrationDeposited crystals were collected by filtration
  3. washwashed with hot water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-983cc726145b4ca9a6c36fb503f52212
Source dataset
uspto-grants-1993_06
Patent number
US05217961

Reaction notes

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