Quinoline, 6-fluoro- → 6-Fluoro-1,2,3,4-tetrahydroquinoline

HRID 1520140ノート

反応式

HRID 1520140 の反応式
C([BH3-])#N.[Na+].[F:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2>C(O)(=O)C>[F:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH2:11][CH2:10][CH2:9]2

参加物

4

反応物 2

HCID 196975Quinoline, 6-fluoro-HCID 5003444Sodium cyanoborohydride

生成物 1

HCID 147839116-Fluoro-1,2,3,4-tetrahydroquinoline収率 71.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Sodium cyanoborohydride (6.45 g, 103 mmol) was added gradually to the solution of 6-fluoro quinoline (5 g, 34 mmol) in glacial acetic acid (100 ml) at ambient temperature. After stirring for 12 h the reaction mixture was quenched in water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water, brine and dried over sodium sulfate, filtered and evaporated in vacuo, the residue was purified by a silica gel column with 1% to 5% ethyl acetate in petroleum ether to afford 6-fluoro-1,2,3,4-tetrahydroquinoline as a light yellow liquid (3.65 g, 71.6%).

後処理

  1. customwas quenched in water
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customthe residue was purified by a silica gel column with 1% to 5% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-c99d7aa46b2e4f6f8d803bc4a4c20492
出典データセット
uspto-grants-2015_07
特許番号
US09073902B2

反応ノート

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