Phenethylamine → 2-(Benzylmethylamino)-5-nitrobenzaldehyde

HRID 48329Notes

Reaction equation

HRID 48329 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:13]([CH2:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:13]([CH2:20][NH:21][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 11430Potassium CarbonateHCID 729332-Chloro-5-nitrobenzaldehyde

Product 1

HCID 227423352-(Benzylmethylamino)-5-nitrobenzaldehydeYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 300 mg (1.62 mmol) of 2-chloro-5-nitrobenzaldehyde, 196 mg (1.62 mmol) of N-benzylmethylamine and 268 mg (1.94 mmol) of potassium carbonate in dimethylformamide was heated at 80° C. for 5 hour. The solvent was removed and the residue was partitioned between water and ethyl acetate (×2). The combined organic phases were evaporated and the residue was purified by column chromatography eluting with 25% ethyl acetate/petroleum ether (40-60° C.) to give 290 mg of 2-(benzylmethylamino)-5-nitrobenzaldehyde as a yellow oil which solidified on standing; MS: m/e 270.9 [M+H]+.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between water and ethyl acetate (×2)
  3. customThe combined organic phases were evaporated
  4. customthe residue was purified by column chromatography
  5. washeluting with 25% ethyl acetate/petroleum ether (40-60° C.)

Sources & evidence

ORD record
ord-91b26239a6804719aa5b83b5fc6a4257
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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