Formaldehyde → 1-(7-chloro-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

HRID 1879645ノート

反応式

HRID 1879645 の反応式
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])=[CH:9][CH:8]=1.[CH2:22]=O>C(O)(=O)C>[Cl:6][C:7]1[CH:8]=[C:9]2[C:10]([CH2:13][CH2:14][N:15]([C:16](=[O:21])[C:17]([F:19])([F:20])[F:18])[CH2:22]2)=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 22292794n-Trifluoroacetyl-4-chlorophenethylamine

生成物 1

HCID 574437351-(7-chloro-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone収率 92.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a mixture of concentrated sulfuric acid (40 mL) and acetic acid (60 mL), N-[2-(4-chlorophenyl)ethyl]-2,2,2-trifluoroacetamide (14.2 g) and paraformaldehyde (2.79 g) were added sequentially and stirred overnight under an argon atmosphere. The reaction mixture was added to ice-cold water, extracted with ethyl acetate, and then washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 7-chloro-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline (13.7 g) as a light-yellow solid.

後処理

  1. additionwere added sequentially
  2. additionThe reaction mixture was added to ice-cold water
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-698ca425df4646fd8c3dc5e5e33ddc99
出典データセット
uspto-grants-2012_11
特許番号
US08318702B2

反応ノート

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