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Ammonium Chloride → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-ylamine

HRID 83307
Notes
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Reaction equation

HRID 83307 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=1.[Cl-].[NH4+]>CO.[Zn]>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[N:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 684447602-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-5-nitro-pyridine

Product 1

HCID 684434446-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-ylamineYield 85%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-5-nitro-pyridine (2.6 g, 83.5 mmol) in methanol (45 mL) was added ammonium chloride (2.23 g, 417.6 mmol) and Zinc (dust, 10.92 g, 167 mmol) and the resulting mixture heated at 70° C. for 1 h. After cooling to room temperature the mixture was filtered and the filtrate evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1) afforded the title compound (2.0 g, 85%) which was obtained as a light yellow oil. MS: m/e=282.0 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationwas filtered
  3. customthe filtrate evaporated
  4. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1)

Sources & evidence

ORD record
ord-5e7c05a2b10242c7a6f3c8b46dab52f3
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846719B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes