N,N-Dimethylethylenediamine → N-(2-(dimethylamino)ethyl)-3-methoxy-4-nitrobenzamide

HRID 1503848Notes

Reaction equation

HRID 1503848 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([OH:8])=O.[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19].O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>ClCCl>[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH:19][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 787643-Methoxy-4-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 68683674N-(2-(dimethylamino)ethyl)-3-methoxy-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxy-4-nitrobenzoic acid (5.0 g, 25.4 mmol) and N1,N1-dimethylethane-1,2-diamine (2.7 g, 30.5 mmol) in dichloromethane (200 mL) were added 1-hydroxybenzotriazole hydrate (7.8 g, 50.8 mmol), 1-ethyl-(3-dimethyl aminopropyl)carbodiimide hydrochloride (9.7 g, 50.8 mmol) and N,N-diisopropyl ethylamine (13.1 g, 101.6 mmol) and the mixture was stirred at ambient temperature for 16 hours. The mixture was washed with water (50 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 20/1 dichloromethane/methanol to give the title compound. MS: 268 (M+H+).

Workup

  1. washThe mixture was washed with water (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  6. washeluting with 20/1 dichloromethane/methanol

Sources & evidence

ORD record
ord-782664ac3f1841289289543018d820c9
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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