Butylamine → 3-(Butylamino)-N-methyl-4-nitrobenzamide

HRID 722416Notes

Reaction equation

HRID 722416 reaction equation
[CH3:1][NH:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6](F)[CH:5]=1.C(N(C(C)C)CC)(C)C.[CH2:24]([NH2:28])[CH2:25][CH2:26][CH3:27]>CN(C=O)C>[CH3:1][NH:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([NH:28][CH2:24][CH2:25][CH2:26][CH3:27])[CH:5]=1

Participants

5

Reactant 3

HCID 8007ButylamineHCID 81531DiisopropylethylamineHCID 21884189HCID 21884189, compound

Product 1

HCID 218841793-(Butylamino)-N-methyl-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-methyl-3-fluoro-4-nitrobenzamide (300 mg, 1.64 mmol) and diisopropylethylamine (0.43 mL, 2.46 mmol) in DMF (7 mL) was added butylamine (0.203 mL, 2.05 mmol) and the solution was stirred at room temperature overnight. The solution was concentrated, the residue dissolved in ethyl acetate and washed with 1 N HCl. The organic phase was dried over MgSO4 and concentrated to give N-methyl-3-butylamino-4-nitrobenzamide as a yellow oil that was used without further purification (380 mg, 92%).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with 1 N HCl
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb3f97fd64f8451f8176831643e18526
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Reaction notes

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