Hydrochloric Acid → 1-[4-Fluoro-2-(methylamino)phenyl]ethanone

HRID 1085917ノート

反応式

HRID 1085917 の反応式
[CH3:1][NH2:2].Cl[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11](=[O:13])[CH3:12].Cl>[Cu].ClCCl>[F:10][C:8]1[CH:7]=[CH:6][C:5]([C:11](=[O:13])[CH3:12])=[C:4]([NH:2][CH3:1])[CH:9]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 27365072'-Chloro-4'-fluoroacetophenone

生成物 1

HCID 199784601-[4-Fluoro-2-(methylamino)phenyl]ethanone

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of a solution of methylamine in industrial methylated spirit (33% w/w; 315.8 ml), industrial methylated spirit (291.6 ml), 2'-chloro-4'-fluoroacetophenone (203.4 g) and copper powder (2.8 g) was heated to 80° in a glass autoclave over a period of 1 hour. The mixture was stirred at 80° for a further 2 hours and then allowed to cool to 45° over a period of 1 hour. The mixture was transferred to a second vessel and the autoclave rinsed with industrial methylated spirit (50 ml) which was then added to the second vessel. The mixture was heated to 50°. A solution of sodium sulphide nonahydrate (11.2 g) in water (117 ml) was added and the mixture was heated at 50° for a further 15 minutes. The mixture was filtered and the residue washed with industrial methylated spirit (100 ml). The filtrate and washings were combined and evaporated to give a brown oil. The brown oil was stirred with hydrochloric acid (5M; 800 ml) for 2.5 hours and then dichloromethane (600 ml) added. The layers were separated and the aqueous phase further extracted with dichloromethane (2×300 ml). The organic phases were combined and evaporated to give 4'-fluoro-2'-(methylamino)acetophenone as a brown oil which solidified at ambient temperature.

後処理

  1. temperaturewas heated to 80° in a glass autoclave over a period of 1 hour
  2. temperatureto cool to 45° over a period of 1 hour
  3. customThe mixture was transferred to a second vessel
  4. washthe autoclave rinsed with industrial methylated spirit (50 ml) which
  5. additionwas then added to the second vessel
  6. temperatureThe mixture was heated to 50°
  7. additionA solution of sodium sulphide nonahydrate (11.2 g) in water (117 ml) was added
  8. temperaturethe mixture was heated at 50° for a further 15 minutes
  9. filtrationThe mixture was filtered
  10. washthe residue washed with industrial methylated spirit (100 ml)
  11. customevaporated
  12. customto give a brown oil
  13. customThe layers were separated
  14. extractionthe aqueous phase further extracted with dichloromethane (2×300 ml)
  15. customevaporated

出典と根拠

ORDレコード
ord-7cd7cef093704b22b289d316663af3d6
出典データセット
uspto-grants-1991_04
特許番号
US05011931

反応ノート

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