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

HRID 1366978Notes

Reaction equation

HRID 1366978 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-fc24602a39bb42ffb310d5b036cbfe70
Source dataset
uspto-grants-2011_02
Patent number
US07893090B2

Reaction notes

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