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

HRID 450446

反応式

HRID 450446 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-23496e601f664a58b0ac285982168897
出典データセット
uspto-grants-2013_07
特許番号
US08486951B2

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