4-Chloro-2-nitro-1-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzene → 5-Chloro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzenamine

HRID 1063937노트

반응식

HRID 1063937 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:4]([N+:16]([O-])=O)[CH:3]=1.[H][H]>[Ni].C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:4]([NH2:16])[CH:3]=1

참가 물질

5

반응물 2

HCID 222762154-Chloro-2-nitro-1-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzeneHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 222752965-Chloro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzenamine수율 98.1%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

A Parr bottle containing 4-chloro-2-nitro-1-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzene (22.6 g, 82.8 mmol) and ethanol (150 mL) was treated with Raney nickel (50% slurry in water, 2.0 g), charged with hydrogen (60 psi) and rocked until hydrogen uptake ceased (3 h). The resultant suspension was filtered through celite, and the celite cake thoroughly washed with fresh ethanol (5×150 mL). The combined organic extracts were concentrated in vacuo to give an orange oil that crystallized on standing. Recrystallization (ethyl acetate/hexane) gave the title compound as a white solid (19.64 g, 98%). 1H NMR (CDCl3) δ7.00 (d, J=8 Hz, 1H), 6.65-6.60 (m, 2H), 4.72 (A of ABq, J=12 Hz, 1H), 4.79-4.77 (m, 1H), 4.45 (B of ABq, J=12 Hz, 1H), 4.27 (bs, 2H), 3.94-3.85 (m, 1H), 3.58-3.50 (m, I), 1.88-1.65 (m, 2H), 1.58-1.46 (m, 4H).

후처리

  1. custom(3 h)
  2. filtrationThe resultant suspension was filtered through celite
  3. washthe celite cake thoroughly washed with fresh ethanol (5×150 mL)
  4. concentrationThe combined organic extracts were concentrated in vacuo
  5. customto give an orange oil
  6. customthat crystallized
  7. customRecrystallization (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0b057d96d1774ee7be2916b89c9e8d5c
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967196B1

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