HCID 58761948, compound → N-methyl-4-ethoxycarbonylmethylaniline

HRID 82290Notes

Reaction equation

HRID 82290 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH:13]=O)=[CH:8][CH:7]=1)[CH3:2]>C1COCC1>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[CH:8][CH:7]=1)[CH3:2]

Participants

3

Reactant 1

HCID 58761948HCID 58761948, compound

Product 1

HCID 11550151N-methyl-4-ethoxycarbonylmethylanilineYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4-formylamino-phenyl)-acetic acid ethyl ester (Preparation 268, 500 mg, 2.41 mmol) in THF (10 mL) was added borane-dimethyl sulphide complex (0.3 mL, 3.13 mmol) at 0° C. and the mixture stirred at room temperature for 1 hour. The reaction mixture was quenched with MeOH (5 mL) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of hexane:EtOAc 100:0 to 75:25) to afford the title compound as an oil in 91% yield, 460 mg.

Workup

  1. customThe reaction mixture was quenched with MeOH (5 mL)
  2. customevaporated in vacuo
  3. customThe crude material was purified by column chromatography on silica gel (gradient of hexane:EtOAc 100:0 to 75:25)

Sources & evidence

ORD record
ord-3c7f5ea79d584507a81b23cc83de28e8
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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