Methanol → HCID 15391208, compound

HRID 619115Notes

Reaction equation

HRID 619115 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[CH2:9][CH:8]=[C:7]2[CH2:15][C:16]([O:18]C)=O.C[OH:21]>O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[C:9](=[O:21])[CH:8]=[C:7]2[CH2:15][CH2:16][OH:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 53661416HCID 53661416, compound

Product 1

HCID 15391208HCID 15391208, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g (79 mmol) of sodium borohydride are added to a suspension of 5.9 g (23.4 mmol) of methyl 6-chloro-1-methyl-1,2-dihydro-4-quinolineacetate in 10 ml of methanol and 100 ml of dry tetrahydrofuran, and the mixture is then heated to reflux for 9 hours. After cooling, the solvents are evaporated off under vacuum and the residue is taken up in 400 ml of dichloromethane and 100 ml of 3 N hydrochloric acid. The organic phase is washed with water, dried over sodium sulphate and filtered and the filtrate is condensed. The crude product is purified by flash chromatography on silica, eluting with a methanol/dichloromethane (5:95) mixture.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureto reflux for 9 hours
  3. temperatureAfter cooling
  4. customthe solvents are evaporated off under vacuum
  5. washThe organic phase is washed with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customcondensed
  9. customThe crude product is purified by flash chromatography on silica
  10. washeluting with a methanol/dichloromethane (5:95) mixture

Sources & evidence

ORD record
ord-0222f207fe94432795f9d78e3b9c08f5
Source dataset
uspto-grants-1999_09
Patent number
US05958924

Reaction notes

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