Methyl Anthranilate → methyl 2-[(4-ethoxy-4-oxobutyl)amino]benzoate

HRID 1457646Notes

Reaction equation

HRID 1457646 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[NH:1][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[O:18][CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 8635Methyl AnthranilateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 266836methyl 2-[(4-ethoxy-4-oxobutyl)amino]benzoate

Procedure

A mixture of 19.2 g of methyl 2-aminobenzoate and 9.6 g of ethyl γ-bromobutyrate is heated at 80°-85° C. for 24 hours, cooled to room temperature and filtered. The solid is washed with CH2Cl2 and the filtrate washed with 1NHCl, H2O, 1NNaHCO3 and brine. The solvent is removed to give an oil. The oil is distilled and the fraction boiling at 45°-75° C. and 130°-160° C. were collected and discarded. The residue is the product (55.4 g of oil)

Workup

  1. temperatureis heated at 80°-85° C. for 24 hours
  2. filtrationfiltered
  3. washThe solid is washed with CH2Cl2
  4. washthe filtrate washed with 1NHCl, H2O, 1NNaHCO3 and brine
  5. customThe solvent is removed
  6. customto give an oil
  7. distillationThe oil is distilled
  8. customthe fraction boiling at 45°-75° C. and 130°-160° C. were collected

Sources & evidence

ORD record
ord-d62bb3baf13843af8b33c6b88aed4eaa
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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