N-cyclopropyl-4-methoxy-2-nitrobenzenamine → HCID 68053640, compound

HRID 1048985Notes

Reaction equation

HRID 1048985 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=2[N+:13]([O-])=O)[CH2:3][CH2:2]1>C(OC(=O)C)C.[Pd]>[CH:1]1([NH:4][C:5]2[C:6]([NH2:13])=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 28536514N-cyclopropyl-4-methoxy-2-nitrobenzenamine

Product 1

HCID 68053640HCID 68053640, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of cyclopropyl-(4-methoxy-2-nitro-phenyl)-amine (0.8 g, 0.0038 mol) in ethylacetate (25 ml) was hydrogenated using 10% Pd/C for 6 h at room temperature. The reaction was filtered through CELITE® and the filter bed was thoroughly washed with EtOAc. The resulting solution was concentrated to provide N1-cyclopropyl-4-methoxy-benzene-1,2-diamine as a brown liquid. C10H14N2O; Crude 1H NMR (400 MHz, DMSO-d6), δ: 6.66 (d, J=8.8 Hz, 1H), 6.18-6.15 (m, 1H), 6.08 (d, J=6.0 Hz, 1H), 4.03 (d, J=6.8 Hz, 1H), 3.75-3.68 (m, 2H), 3.58 (s, 3H), 0.63 (d, J=6.0 Hz, 2H), 0.40 (s, 2H). MS (M+1): 179.2.

Workup

  1. customfor 6 h
  2. customat room temperature
  3. filtrationThe reaction was filtered through CELITE®
  4. washthe filter bed was thoroughly washed with EtOAc
  5. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-e08862409b51468aa3bbba27b103f205
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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