5-[2-(2,5-Dimethoxyphenyl)ethyl]-2-amino benzoic acid methylester → 5-[2-(2,5-Dimethoxyphenyl)ethyl]-2-methoxycarbonylamino Benzoic acid Methylester

HRID 1603535Notes

Reaction equation

HRID 1603535 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[O:20][CH3:21])[CH:7]=[CH:6][C:5]=1[NH2:22]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[O:20][CH3:21])[CH:7]=[CH:6][C:5]=1[NH:22][C:3]([O:2][CH3:1])=[O:23]

Participants

4

Reactant 1

HCID 544614515-[2-(2,5-Dimethoxyphenyl)ethyl]-2-amino benzoic acid methylester

Product 1

HCID 543092215-[2-(2,5-Dimethoxyphenyl)ethyl]-2-methoxycarbonylamino Benzoic acid Methylester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 115 mg of 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-amino benzoic acid methylester and 50 mg of 4-dimethylaminopyridine in 6 ml of dry dichloromethane is treated with 35 mg of methyl chloroformiate and stirred for 3 hours at room temperature. Then the mixture is poured onto aqueous pH7 buffer solution and extracted with ethyl acetate. The combined organic extracts are dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate=8/1) to yield the title compound as colourless crystals. mp: 80-82°.

Workup

  1. additionis treated with 35 mg of methyl chloroformiate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts are dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by silica gel chromatography (cyclohexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-dc304a7e6df74c3d8a8b730cbcae6740
Source dataset
uspto-grants-1999_11
Patent number
US05990116

Reaction notes

Loading…