3-Nitro-4-(propylamino)benzonitrile → 3-Amino-4-(propylamino)benzonitrile

HRID 1988696Notes

Reaction equation

HRID 1988696 reaction equation
[CH2:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[N+:13]([O-])=O)[CH2:2][CH3:3]>C(OCC)(=O)C.[Pd]>[NH2:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[NH:4][CH2:1][CH2:2][CH3:3])[C:9]#[N:10]

Participants

4

Reactant 1

HCID 230793333-Nitro-4-(propylamino)benzonitrile

Product 1

HCID 223802993-Amino-4-(propylamino)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a Parr bottle containing 4-n-propylamino-3-nitrobenzonitrile (7.63 g, 37.2 mmol) in ethyl acetate (38 mL) is added 5% Pd/C (50% wet, 633 mg). The Parr bottle is sealed in a mechanical shaker, evacuated, and then purged with nitrogen followed by hydrogen. The system is pressurized to 50 PSI of hydrogen at room temperature and mechanical shaking engaged. After 2 hours, shaking is stopped, and the system purged with nitrogen prior to opening the vessel. The reaction mixture is filtered through celite, concentrated in vacuo, and the obtained solid recrystallized by dissolving in ethyl acetate (15 mL), heating, and adding hexanes (15 mL), to give 3-Amino-4-n-propylaminobenzonitrile as gray crystals. 1H NMR (CDCl3) δ 7.14 (1H, dd), 6.92 (1H, d), 6.56 (1H, d), 3.98 (1H, br s), 3.30 (2H, br s), 3.12 (2H, t), 1.75-1.65 (2H, m), 1.03 (3H, t). LRMS calcd 175.23, found 176.2 (MH+).

Workup

  1. customThe Parr bottle is sealed in a mechanical shaker
  2. customevacuated
  3. custompurged with nitrogen
  4. customis pressurized to 50 PSI of hydrogen at room temperature
  5. stirringshaking
  6. customthe system purged with nitrogen
  7. filtrationThe reaction mixture is filtered through celite
  8. concentrationconcentrated in vacuo
  9. customthe obtained solid recrystallized
  10. dissolutionby dissolving in ethyl acetate (15 mL)
  11. temperatureheating
  12. additionadding hexanes (15 mL)

Sources & evidence

ORD record
ord-b6c435f936634b47bb762a81ab96ab16
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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