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 1063937ノート

反応式

HRID 1063937 の反応式
[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

参加物

5

反応物 2

HCID 222762154-Chloro-2-nitro-1-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzeneHCID 178418361HCID 178418361、化合物2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0b057d96d1774ee7be2916b89c9e8d5c
出典データセット
uspto-grants-2005_11
特許番号
US06967196B1

反応ノート

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