Ammonium Chloride → 5-(2-Chloropyridin-4-yloxy)pyridin-2-amine

HRID 450446

반응식

HRID 450446 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[Cl-].[NH4+]>C1COCC1.CO.[Zn]>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[N:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

생성물 1

HCID 593227885-(2-Chloropyridin-4-yloxy)pyridin-2-amine수율 103%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

2-Chloro-4-(6-nitropyridin-3-yloxy)pyridine (0.540 g, 2.146 mmol) was dissolved in THF (54 ml) and MeOH (54 ml). Ammonium chloride (1.148 g, 21.46 mmol) was then added, followed by zinc dust (1.403 g, 21.46 mmol). The reaction was stirred at RT for 45 minutes, filtered over Celite® and concentrated under reduced pressure to yield 5-(2-chloropyridin-4-yloxy)pyridin-2-amine as a brown solid (0.49 g, 99%). It was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): δ 8.46 (d, 1H), 7.81 (d, 1H), 7.30 (dd, 1H), 6.90 (m, 2H), 6.50 (d, 1H), 6.08 (s, 2H); MS (ESI) m/z: 222.0 (M+H+).

후처리

  1. filtrationfiltered over Celite®
  2. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-23496e601f664a58b0ac285982168897
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486951B2

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