Ammonium Chloride → HCID 90410944, compound

HRID 626513Notes

Reaction equation

HRID 626513 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-]>CO.C1COCC1.[Zn]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH:12]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 90410860HCID 90410860, compound

Product 1

HCID 90410944HCID 90410944, compoundYield 222%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)propionamide (0.513 g, 1.780 mmol) in MeOH (10 mL) and THF (10 mL) was treated with NH4Cl (3.81 g, 71.2 mmol) followed by zinc dust (1.164 g, 17.80 mmol) and stirred at RT overnight. Additional zinc dust (1 g) was added the mixture stirred at RT for 2 days. The solids were removed via filtration, washed with THF and filtrate concentrated to dryness. The material was suspended in THF, sonicated, the resulting solid removed via filtration and the filtrate concentrated to dryness to afford crude N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)propionamide (1.02 g, 222%) which was carried on without further purification. MS (ESI) m/z: 259.1 (M+H+).

Workup

  1. stirringstirred at RT for 2 days
  2. customThe solids were removed via filtration
  3. washwashed with THF and filtrate
  4. concentrationconcentrated to dryness
  5. customsonicated
  6. customthe resulting solid removed via filtration
  7. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-2c5e22d992184d62a63635edb7a40ab3
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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