3-(dimethylamino)-N-(3-nitrophenyl)propanamide → N-(3-Aminophenyl)-3-(dimethylamino)propanamide

HRID 716856Notes

Reaction equation

HRID 716856 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)=[O:6]>[Pd].C(OCC)(=O)C>[NH2:14][C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][CH2:3][N:2]([CH3:17])[CH3:1])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 866899623-(dimethylamino)-N-(3-nitrophenyl)propanamide

Product 1

HCID 16781477N-(3-Aminophenyl)-3-(dimethylamino)propanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on charcoal (1.0 g) was suspended in a solution of 3-(dimethylamino)-N-(3-nitrophenyl)propanamide (4.7 g, 20 mmol) in ethyl acetate. The mixture was hydrogenated at 35 psi overnight. The reaction mixture was filtered through a pad of Celite. The filter cake was washed successively with ethyl acetate and methanol. The combined filtrate and washings were evaporated in vacuo to dryness to give N-(3-aminophenyl)-3-(dimethylamino)propanamide as brown gum, 3.9 g (94%). 1H NMR (DMSO-d6) δ: 2.16 (6H, s, CH3), 2.36 (2H, t, J=6.8 Hz, CH2), 3.40 (2H, t, J=6.8 Hz, CH2), 5.20 (2H, brs, NH2), 6.66 (1H, d, J=7.8 Hz, Ar—H), 6.91 (1H, d, J=7.7 Hz, Ar—H), 7.04 (1H, s, Ar—H), 7.15 (1H, t, J=7.4 Hz, Ar—H), 9.05-9.08 (1H, brs, NH).

Workup

  1. customwas hydrogenated at 35 psi overnight
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. washThe filter cake was washed successively with ethyl acetate and methanol
  4. customThe combined filtrate and washings were evaporated in vacuo to dryness

Sources & evidence

ORD record
ord-8c2b3da08af64b6eb68b8cafbf7fab93
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

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