3-(4-Amino-5-nitro-2'-trifluoromethyl-biphenyl-3-yl)-prop-2-yn-1-ol → 3-(4,5-Diamino-2'-trifluoromethyl-biphenyl-3-yl)-propan-1-ol

HRID 1518129노트

반응식

HRID 1518129 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])=[CH:4][C:3]=1[C:21]#[C:22][CH2:23][OH:24]>[Pd].C(O)C>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:18])([F:19])[F:20])=[CH:4][C:3]=1[CH2:21][CH2:22][CH2:23][OH:24]

참가 물질

4

반응물 1

HCID 509943603-(4-Amino-5-nitro-2'-trifluoromethyl-biphenyl-3-yl)-prop-2-yn-1-ol

생성물 1

HCID 592800973-(4,5-Diamino-2'-trifluoromethyl-biphenyl-3-yl)-propan-1-ol수율 73%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매2회

실험 절차

3-(4-Amino-5-nitro-2′-trifluoromethyl-biphenyl-3-yl)-prop-2-yn-1-ol (148 mg, 0.440 mmol, as prepared in the previous step) was placed in an 8 mL vial equipped with a magnetic stir bar, and dry EtOH (2 mL) was added via syringe. To the ethanol solution was added 10% Pd on activated carbon (27 mg), and the vial was capped with a rubber septum. Hydrogen gas was bubbled through the stirred solution for 3 min, and the reaction was stirred under an atmosphere of H2 at 1 atm for 16 h. The vial was vented, the reaction was filtered, and the filter was washed three times with MeOH (5 mL). The solvent was removed under reduced pressure to give 101 mg (73%) of the desired compound. 1H-NMR (400 MHz, CDCl3) δ: 7.68 (d, J=7.6 Hz, 1H), 7.48 (t, J=7.3 Hz, 1H), 7.38 (t, J=7.6 Hz, 1H), 7.30 (d, J=7.6 Hz, 1H), 6.61 (s, 1H), 6.60 (s, 1H), 3.65 (t, J=5.9 Hz, 2H), 3.48 (br. s., 4H), 2.66 (t, J=7.3 Hz, 2H), 1.86 (quin, J=6.6 Hz, 2H).

후처리

  1. customvial equipped with a magnetic stir bar
  2. customthe vial was capped with a rubber septum
  3. customHydrogen gas was bubbled through the stirred solution for 3 min
  4. filtrationthe reaction was filtered
  5. washthe filter was washed three times with MeOH (5 mL)
  6. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-532b6d2556194d13b2b6f6a0769b8662
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232409B2

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