Cyclopropanemethanamine → N-Cyclopropylmethyl-2-ethyl-5-nitro-benzamide

HRID 47443Notes

Reaction equation

HRID 47443 reaction equation
[CH2:1]([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)[CH3:2].CCN=C=NCCCN(C)C.Cl.[CH:27]1([CH2:30][NH2:31])[CH2:29][CH2:28]1.OC1C2N=NNC=2C=CC=1>CN(C)C=O>[CH:27]1([CH2:30][NH:31][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:3]=2[CH2:1][CH3:2])[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 75646CyclopropanemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 227451732-Ethyl-5-nitrobenzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 22745137N-Cyclopropylmethyl-2-ethyl-5-nitro-benzamideYield 78.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Ethyl-5-nitrobenzoic acid (0.40 g), EDC.HCl (0.45 g), cyclopropylmethylamine (0.17 g) and hydroxybenzotriazole (0.04 g) were combined in dimethylformamide (10 ml) and stirred for 18 h. Solvent was removed at reduced pressure, the residue dissolved in dichloromethane and washed with 2N HCl and water. The organic phase was dried (MgSO4) and solvent removed at reduced pressure to give the title compound (0.4 g). 1H NMR (CDCl3) δ: 0.31 (2H, m), 0.59 (2H, m), 1.09 (1H, m), 1.28(3H, t, J=7.6Hz), 2.92 (2H, m), 3.33 (2H, m), 5.97 (1H, brs), 7.45 (1H, d, J=8.4 Hz), 8.20 (2H, m).

Workup

  1. customSolvent was removed at reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with 2N HCl and water
  4. dry with materialThe organic phase was dried (MgSO4) and solvent
  5. customremoved at reduced pressure

Sources & evidence

ORD record
ord-b09d54507eae4f79bde74c00241c56d9
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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