Water → HCID 22161782, compound

HRID 1088789Notes

Reaction equation

HRID 1088789 reaction equation
[C:1]([BH3-])#N.[Na+].[OH:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[CH3:17].O>O1CCCC1.C(O)=O>[CH3:1][N:15]1[C:16]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][OH:5])[C:12]([CH3:17])=[CH:13][CH2:14]1

Participants

6

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 22161790HCID 22161790, compound

Product 1

HCID 22161782HCID 22161782, compoundYield 23.5%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium cyanoborohydride (7.9 g) was dissolved in tetrahydrofuran (50 ml). After adding and dissolving 8-hydroxymethyl-4-methylquinoline (3.5 g) in the solution, formic acid (50 ml) was added dropwise thereto with stirring under ice-cooling in nitrogen stream. The mixture was stirred for 5 hours at room temperature. After completion of the reaction, water was added to the reaction mixture and the mixture was concentrated under reduced pressure. The resulting residue was adjusted to alkalinic with a sodium hydroxide aqueous solution and extracted with chloroform. After drying the extract over anhydrous magnesium sulfate, chloroform was distilled off. The resulting residue was purified by silica gel column chromatography [eluent: dichloromethane-methanol(200:1)], then 1,4-dimethyl-8-hydroxymethyl-1,2-dihydroquinoline (0.9 g) was obtained.

Workup

  1. additionAfter adding
  2. additionwas added dropwise
  3. temperaturecooling in nitrogen stream
  4. stirringThe mixture was stirred for 5 hours at room temperature
  5. additionwas added to the reaction mixture
  6. concentrationthe mixture was concentrated under reduced pressure
  7. extractionextracted with chloroform
  8. customAfter drying the
  9. extractionextract over anhydrous magnesium sulfate, chloroform
  10. distillationwas distilled off
  11. customThe resulting residue was purified by silica gel column chromatography [eluent: dichloromethane-methanol(200:1)]

Sources & evidence

ORD record
ord-5f20e630af264330b16de0806df10ebe
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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