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

HRID 450446

Reaction equation

HRID 450446 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-23496e601f664a58b0ac285982168897
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Linked notes

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