Methanol → HCID 14390617, compound

HRID 1904965Notes

Reaction equation

HRID 1904965 reaction equation
[CH2:1]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH3:19])[C:10]=1[C:20](=[O:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(O)(C)C.CO>O>[CH2:1]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH3:19])[C:10]=1[CH:20]([CH3:21])[OH:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 14390616HCID 14390616, compound

Product 1

HCID 14390617HCID 14390617, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution prepared from 1-(4-benzylamino-2-methyl-3-quinolinyl)-ethanone (4 g), sodium borohydride (1 g), 75 ml of isopropanol and 25 ml of methanol was stirred one hour at 45°, cooled, stirred with 500 ml of water and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride and dried over anhydrous sodium sulfate, filtered and evaporated to 4 g of solid. This material was purified by flash chromatography (silica, 10% methanol in dichloromethane) to give 3.6 g of solid, mp 176°-177°.

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water and saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated to 4 g of solid
  8. customThis material was purified by flash chromatography (silica, 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4c8e9c32561549c2a5ebf1b06633d933
Source dataset
uspto-grants-1989_06
Patent number
US04840972

Reaction notes

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