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

HRID 1426166노트

반응식

HRID 1426166 반응식
[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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1656dbb393d24203a6b5c7cd91069b6a
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

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