Ethanol → 2-Amino-4-methoxy-biphenyl

HRID 617406노트

반응식

HRID 617406 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([N+:15]([O-])=O)[CH:4]=1.C(O)C>[Ni].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 702EthanolHCID 114019374-Methoxy-2-nitro-biphenyl

생성물 1

HCID 27603632-Amino-4-methoxy-biphenyl수율 100.4%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 962Water용매

실험 절차

A Parr bottle charged with 4-methoxy-2-nitrobiphenyl (27.6 g, 120 mmol), Raney nickel (1.5 g), ethanol (100 mL), and H2O (100 mL) was rocked under hydrogen (60 psi) for 3 h. The suspension was filtered through Celite, the cake washed with ethanol (500 mL) and tetrahydrofuran (500 mL), and the filtrate concentrated in vacuo. The residual suspension was digested with CH2Cl2 (300 mL), washed with H2O (300 mL), and the organic portion extracted with 1 N HCl (4×200 mL). The combined extracts were made basic with 50% NaOH, extracted with CH2Cl2 (3×200 mL), and the organic extracts washed with brine (300 mL), dried (K2CO3), filtered, and concentrated in vacuo to give 24 g (100%) of the title compound which was used without further purification: 1H NMR (300 MHz, CDCl3) δ 3.78 (s, 3H), 3.90 (br s, 2H), 6.34 (d, J=2 Hz, 1H), 6.41 (dd, J=8, 2 Hz, 1H), 7.03 (d, J=8 Hz, 1H), 7.15-7.33 (m, 2H), 7.36-7.41 (m, 3H).

후처리

  1. filtrationThe suspension was filtered through Celite
  2. washthe cake washed with ethanol (500 mL) and tetrahydrofuran (500 mL)
  3. concentrationthe filtrate concentrated in vacuo
  4. washwashed with H2O (300 mL)
  5. extractionthe organic portion extracted with 1 N HCl (4×200 mL)
  6. extractionextracted with CH2Cl2 (3×200 mL)
  7. washthe organic extracts washed with brine (300 mL)
  8. dry with materialdried (K2CO3)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8ca26cf393ad4aa7b71f1a7fdbb284a2
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05948817

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