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

HRID 895511ノート

反応式

HRID 895511 の反応式
[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]

参加物

4

反応物 1

HCID 230793333-Nitro-4-(propylamino)benzonitrile

生成物 1

HCID 223802993-Amino-4-(propylamino)benzonitrile

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-49755a26f9b54c23b45f89fb03415f57
出典データセット
uspto-grants-2005_07
特許番号
US06916819B2

反応ノート

読み込み中…