Ammonium Hydroxide → 4-[(3,6-Dichloropyridin-2-yl)methoxy]aniline

HRID 1730018Notes

Reaction equation

HRID 1730018 reaction equation
[Cl:1][C:2]1[C:3]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17]C(=O)C)=[CH:13][CH:12]=2)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[OH-].[NH4+]>B(F)(F)F.CO>[Cl:1][C:2]1[C:3]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 20366210N-{4-[(3,6-Dichloropyridin-2-yl)methoxy]phenyl}acetamide

Product 1

HCID 203661734-[(3,6-Dichloropyridin-2-yl)methoxy]aniline

Reagents, catalysts & solvents 1

HCID 11062313Boron, trifluoro(methanol)-, (T-4)-Solvent

Procedure

N-(4-((3,6-Dichloro-2-pyridinyl)methoxy)phenyl)acetamide (30.27 grams; 0.097 mole) was mixed with a 170 ml. solution of boron trifluoride-methanol (1 gram per 10 ml.) and the resulting reaction mixture refluxed for a period of 4 1/2 hours. The reaction mixture was then diluted and cooled with ice water to a temperature of between about 0° to about 10° C. Concentrated ammonium hydroxide was added until the reaction mixture was basic. The reaction mixture was then extracted with portions of methylene chloride, the extracts combined and the solvent removed by evaporation. The residue thus obtained was extracted with five 500 ml. portions of hexane. The crystalline material which precipitated from the hexane mixture upon cooling was recovered by filtration. As a result of these operations, the desired 4-((3,6-dichloro-2-pyridinyl)methoxy)benzenamine compound was recovered as a light yellow crystalline solid having a melting point of 74°-75° C.

Workup

  1. temperaturerefluxed for a period of 4 1/2 hours
  2. additionThe reaction mixture was then diluted
  3. extractionThe reaction mixture was then extracted with portions of methylene chloride
  4. customthe solvent removed by evaporation
  5. customThe residue thus obtained
  6. extractionwas extracted with five 500 ml
  7. customThe crystalline material which precipitated from the hexane mixture
  8. temperatureupon cooling
  9. filtrationwas recovered by filtration
  10. customAs a result of these operations
  11. customthe desired 4-((3,6-dichloro-2-pyridinyl)methoxy)benzenamine compound was recovered as a light yellow crystalline solid

Sources & evidence

ORD record
ord-406d7e12f2864f4dac9cb4ce6a1d3ecb
Source dataset
uspto-grants-1976_11
Patent number
US03991068

Reaction notes

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