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

HRID 1415122

反応式

HRID 1415122 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

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

実験手順

N-(4-((3,6-Dichloro-2-pyridinyl)methoxy)phenyl)acetamide (30.27 grams; 0.097 mole) was mixed with a 270 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.

後処理

  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

出典と根拠

ORDレコード
ord-ef8ea39bde8b463fa6fa7977bb5996ae
出典データセット
uspto-grants-1977_01
特許番号
US04003906

関連ノート

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