Potassium borohydride → HCID 19039850, compound

HRID 1684540Notes

Reaction equation

HRID 1684540 reaction equation
C([CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[N:4]1[C:15]([O:17][CH2:18]C)=[O:16])=O.[BH4-].[K+]>CO.O.C1(C)C=CC=CC=1>[CH3:14][O:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]1[C:15](=[O:16])[O:17][CH2:18][CH:3]1[CH2:12][CH2:11]2

Participants

6

Reactant 2

HCID 4192641Potassium borohydrideHCID 19039853HCID 19039853, compound

Product 1

HCID 19039850HCID 19039850, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 10.9 g (41.4 mmol) of ethyl 2-formyl-6-methoxy-1,2,3,4-tetrahydroquinoline-1-carboxylate in 100 ml of methanol, cooled to 0° C., are added portionwise 2.2 g (41.4 mmol) of potassium borohydride. The medium is stirred for 1 h and then hydrolyzed, diluted with water and extracted with diethyl ether. The organic phase is then washed with water and dried over sodium sulphate, and the solvent is evaporated off under reduced pressure. The oil obtained is redissolved in 90 ml of toluene, the solution is heated to reflux in order to remove traces of water, and a catalytic amount of 10% sodium methoxide in methanol is then added at 90° C. The mixture is again heated to reflux in order to remove the ethanol formed, followed by evaporation of the solvent. The residue is taken up in ethyl acetate and washed with water, then the organic phase is dried over sodium sulphate and concentrated under reduced pressure. After chromatography on a column of silica with a 4/1 mixture of heptane and ethyl acetate, 5.0 g of product are obtained.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase is then washed with water
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is evaporated off under reduced pressure
  5. customThe oil obtained
  6. temperaturethe solution is heated
  7. temperatureto reflux in order
  8. customto remove traces of water
  9. additiona catalytic amount of 10% sodium methoxide in methanol is then added at 90° C
  10. temperatureThe mixture is again heated
  11. temperatureto reflux in order
  12. customto remove the ethanol
  13. customformed
  14. customfollowed by evaporation of the solvent
  15. washwashed with water
  16. dry with materialthe organic phase is dried over sodium sulphate
  17. concentrationconcentrated under reduced pressure
  18. additionAfter chromatography on a column of silica with a 4/1 mixture of heptane and ethyl acetate, 5.0 g of product
  19. customare obtained

Sources & evidence

ORD record
ord-3f2df7263bf6438e990f8e2631c74b8e
Source dataset
uspto-grants-1997_06
Patent number
US05641785

Reaction notes

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