Dimethylamine → 2-Amino-N,N-dimethyl-3-nitrobenzamide

HRID 2077367Notes

Reaction equation

HRID 2077367 reaction equation
C[CH2:2][N:3]=[C:4]=NCCCN(C)C.Cl.[NH2:13][C:14]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].CNC.C1COCC1>ClCCl.ON1C2C=CC=CC=2N=N1>[NH2:13][C:14]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([N:3]([CH3:4])[CH3:2])=[O:17]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 2196332-Amino-3-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 587361062-Amino-N,N-dimethyl-3-nitrobenzamideYield 100%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 6344DichloromethaneSolvent

Procedure

EDC.HCl (2.47 g, 12.88 mmol) was added to a stirred mixture of 2-amino-3-nitrobenzoic acid (2.18 g, 11.98 mmol) (Mickelson, J. Med. Chem, 39(23) 4662 (1996)), 2M dimethylamine in THF (6.45 ml, 12.9 mmol) and 1-hydroxybenzotriazole (0.1 g, 0.74 mmol) in dichloromethane (100 ml). The reaction mixture was stirred at room temperature for 18 h, washed with saturated aqueous sodium bicarbonate and the organic layer dried (Na2SO4) and evaporated in vacuo to afford the title compound as a pale orange gum (2.5 g, 100%).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialthe organic layer dried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-4bb88b80c5b94c11888c66872974ab88
Source dataset
uspto-grants-2011_04
Patent number
US07928125B2

Reaction notes

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