Water → HCID 12511634, compound

HRID 907373Notes

Reaction equation

HRID 907373 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=[C:3]1[CH:10]=[O:11].[BH4-].[Na+].O>C(O)C>[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[CH:4]=[C:3]1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 123454411-Methyl-4-nitro-1H-pyrrole-2-carbaldehyde

Product 1

HCID 12511634HCID 12511634, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Methyl-4-nitro-1H-pyrrole-2-carbaldehyde (0.400 g, 2.08 mmol; see step (i) above) was placed in 50 mL of anhydrous ethanol under N2. NaBH4 (0.040 g, 1.04 mmol) was added in small portions over 5 min and the solution allowed to stir for 20 min. Water (10 mL) was added slowly to quench the reaction. The organics were then extracted with ethyl acetate (2×20 mL) and the resultant organic fractions dried (MgSO4), filtered and the solvent removed under reduced pressure to yield the sub-title compound as a light brown solid (0.318 g, 98%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe organics were then extracted with ethyl acetate (2×20 mL)
  4. dry with materialthe resultant organic fractions dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ad0672c05bb24297b3e39cfa84f5484a
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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