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

HRID 895511

반응식

HRID 895511 반응식
[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]

참가 물질

4

반응물 1

HCID 230793333-Nitro-4-(propylamino)benzonitrile

생성물 1

HCID 223802993-Amino-4-(propylamino)benzonitrile

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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. customrecrystallized
  10. dissolutionby dissolving in ethyl acetate (15 mL)
  11. temperatureheating
  12. additionadding hexanes (15 mL)

출처 및 근거

ORD 기록
ord-49755a26f9b54c23b45f89fb03415f57
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916819B2

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