Chloroform → HCID 54265149, compound

HRID 2247878Notes

Reaction equation

HRID 2247878 reaction equation
[C:1]([C:4]1[C:5]([CH3:30])=[N:6][C:7]([C:19](=[O:29])[NH:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)(=[O:3])[CH3:2].[BH4-].[Na+].C(Cl)(Cl)Cl>CO>[OH:3][CH:1]([C:4]1[C:5]([CH3:30])=[N:6][C:7]([C:19](=[O:29])[NH:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 19815989HCID 19815989, compound

Product 1

HCID 54265149HCID 54265149, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-acetyl-2-methyl-6-(2-morpholinoethylcarbamoyl)-4-(3-nitrophenyl)pyridine (3 g) in methanol (30 ml) was added sodium borohydride (0.28 g) under ice-cooling. After stirring for 1 hour at same temperature, the solution was poured into a mixture of ice water (50 ml) and chloroform (50 ml). The organic layer was washed with brine and dried over magnesium sulfate. After evaporating the solvent, the residue was recrystallized from a mixture of ethanol and ethyl acetate to give 3-(1-hydroxyethyl)-2-methyl-6-(2-morpholinoethylcarbamoyl)-4- (3-nitrophenyl)pyridine (1.53 g).

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporating the solvent
  5. customthe residue was recrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-2a75f02e65a84a9295578e0db14f88e2
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

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