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

HRID 1520140Notes

Reaction equation

HRID 1520140 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 147839116-Fluoro-1,2,3,4-tetrahydroquinolineYield 71.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-c99d7aa46b2e4f6f8d803bc4a4c20492
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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