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

HRID 2060707Notes

Reaction equation

HRID 2060707 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:16]([O-])=O)=[CH:13][C:14]=2[CH3:15])[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[C:14]([CH3:15])=[CH:13][C:12]([NH2:16])=[N:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 866416892-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine

Product 1

HCID 866416905-(2-Chloropyridin-4-yloxy)-4-methylpyridin-2-amineYield 103%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine was dissolved in THF (11.95 ml)/methanol (11.95 ml) and ammonium chloride (0.256 g, 4.78 mmol) was added, followed by zinc dust (0.313 g, 4.78 mmol). The mixture stirred at RT for 1.5 hours before it was filtered through Celite®. The filtrate was evaporated under reduced pressure to yield a magenta film which was partitioned between ethyl acetate/THF (4:1) and water. The organic layer was washed with brine, dried (MgSO4) and evaporated to yield 5-(2-chloropyridin-4-yloxy)-4-methylpyridin-2-amine as a brown oil (0.116 g, 103%), which was used in the next step without purification. MS (ESI) m/z: 236.1 (M+H+).

Workup

  1. additionwas added
  2. filtrationwas filtered through Celite®
  3. customThe filtrate was evaporated under reduced pressure
  4. customto yield a magenta film which
  5. customwas partitioned between ethyl acetate/THF (4:1) and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-139e7913f7c742a5a6b8d06dbaa10217
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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