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 1518129ノート

反応式

HRID 1518129 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-532b6d2556194d13b2b6f6a0769b8662
出典データセット
uspto-grants-2012_07
特許番号
US08232409B2

反応ノート

読み込み中…