4-Methyl-3-nitroaniline → N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide

HRID 1921285

Reaction equation

HRID 1921285 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([C:15](O)=[O:16])[CH2:14][CH2:13]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:15]([CH:12]2[CH2:14][CH2:13]2)=[O:16])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 83904-Methyl-3-nitroanilineHCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 4104437N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamideYield 93.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-methyl-3-nitrophenyl)amine (304 mg) in DMF (3 mL) were added cyclopropanecarboxylic acid (258 mg), HATU (1.14 g) and iPr2NEt (1.55 g) successively, and the mixture was stirred at room temperature for 16 hr under a nitrogen atmosphere. The reaction mixture was diluted with EtOAc (15 mL) and the resulted mixture was washed with 1 M HCl (15 mL×2), saturated aqueous NaHCO3 (15 mL×2) and brine, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with EtOAc-hexane (1:2) to give N-(4-methyl-3-nitrophenyl)cyclopropanecarboxamide (413 mg).

Workup

  1. washthe resulted mixture was washed with 1 M HCl (15 mL×2), saturated aqueous NaHCO3 (15 mL×2) and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with EtOAc-hexane (1:2)

Sources & evidence

ORD record
ord-bca658655c604b3d9c42e3007194f17b
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Linked notes

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