3-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine → 3-(Benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amine

HRID 1426166ノート

反応式

HRID 1426166 の反応式
[CH2:1]([O:8][C:9]1[C:10]([N+:23]([O-])=O)=[N:11][CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.ClCCl.[Zn]>[CH2:1]([O:8][C:9]1[C:10]([NH2:23])=[N:11][CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 1

HCID 673694033-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine

生成物 1

HCID 673705813-(Benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amine収率 98.7%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

Zinc (1.34 g, 20.5 mmol) was added slowly to a solution of 3-(benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine (0.730 g, 2.05 mmol) in acetic acid (20 mL) in a water bath. The reaction mixture was stirred 2 hours, then diluted with dichloromethane (100 mL) and filtered through Celite. The pad was washed several times with dichloromethane, and the combined filtrates were concentrated. The residue was partitioned between ethyl acetate and 2N NaOH, and the organic layer was washed with brine, dried, and concentrated to afford 3-(benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amine (0.66 g, 98.7% yield) as a light yellow oil. 1H NMR (CDCl3) δ 4.85 (bs, 2H), 5.03 (s, 2H), 6.79-6.83 (m, 2H), 7.02 (t, 1H), 7.14 (t, 1H), 7.37-7.47 (m, 7H).

後処理

  1. filtrationfiltered through Celite
  2. washThe pad was washed several times with dichloromethane
  3. concentrationthe combined filtrates were concentrated
  4. customThe residue was partitioned between ethyl acetate and 2N NaOH
  5. washthe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1656dbb393d24203a6b5c7cd91069b6a
出典データセット
uspto-grants-2015_01
特許番号
US08933077B2

反応ノート

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