6-Methoxyquinoline → Quinoline, 1,2,3,4-tetrahydro-6-methoxy-

HRID 1815903Notes

Reaction equation

HRID 1815903 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[BH3-]C#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 148606-MethoxyquinolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67113Quinoline, 1,2,3,4-tetrahydro-6-methoxy-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Based on G. W. Gribble, et al., Synthesis, 1975, 650-652, 6-methoxyquinoline (1.26 g, 7.9 mmol) was dissolved in glacial acetic acid (20 mL) under N2 at RT. Solid NaCNBH3 (2 g, 32 mmol) was added in small portions over a 45 min period. The reaction was heated to 50° C. for 8 h, then cooled to RT and stirred overnight. The reaction was quenched by cooling it to 0° C., and the pH of the solution was adjusted to 14 with 2 N NaOH. The solution was extracted 3 times with EtOAc. The EtOAc extracts were washed brine, combined, dried over Na2SO4, filtered, and concentrated, then eluted through a 17×2.5 cm column of silica gel (5% and 10% EtOAc/Hexane step gradient) giving 6-methoxy-1,2,3,4-tetrahydroquinoline as a red oil. This material was used without further purification.

Workup

  1. temperaturecooled to RT
  2. customThe reaction was quenched
  3. temperatureby cooling it to 0° C.
  4. extractionThe solution was extracted 3 times with EtOAc
  5. washThe EtOAc extracts were washed brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washeluted through a 17×2.5 cm column of silica gel (5% and 10% EtOAc/Hexane step gradient)

Sources & evidence

ORD record
ord-89fa0e5892d147d691fa5ac6b2359a61
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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