Cyclopropanemethanamine → N-cyclopropylmethyl-2-methoxy-5-nitrobenzamide

HRID 47447Notes

Reaction equation

HRID 47447 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH:15]1([CH2:18][NH2:19])[CH2:17][CH2:16]1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH:15]1([CH2:18][NH:19][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:3]=2[O:2][CH3:1])[CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 75646CyclopropanemethanamineHCID 757711-HydroxybenzotriazoleHCID 2841632-Methoxy-5-nitrobenzoic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22745177N-cyclopropylmethyl-2-methoxy-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-methoxy-5-nitrobenzoic acid (4.9 g) (Rec. Trav. Chim. Pays-Bas, 1936, 737) and cyclopropylmethylamine (1.75 g) in dimethylformamide was treated with N-hydroxybenzotriazole (0.2 g) and EDC.HCl (4.74 g). The mixture was stirred for 24 h. Saturated sodium hydrogen carbonate was added, the mixture stirred for 3 h and the precipitate collected as the title compound (6.95 g). m/z (API+): 251 (MH+).

Workup

  1. stirringthe mixture stirred for 3 h
  2. customthe precipitate collected as the title compound (6.95 g)

Sources & evidence

ORD record
ord-3370e82ed778478a89ecbc5d7a072618
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

Loading…