2-morpholino-5-nitrobenzaldehyde → HCID 2727950, compound

HRID 1783941Notes

Reaction equation

HRID 1783941 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=2[CH:9]=[O:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[N:1]1([C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=2[CH2:9][OH:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 27948722-morpholino-5-nitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2727950HCID 2727950, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled (0° C.) solution of 2-morpholin-4-yl-5-nitro-benzaldehyde (0.8 g, 3.39 mmol) in MeOH (5 mL) is added NaBH4 (0.125 g, 3.39 mmol) and the reaction mixture is stirred at room temperature for 3 hours. After quenching the reaction with water, the solvent is removed in vacuo and the residue dissolved in ethyl acetate and washed with brine. The organic layer is dried over MgSO4, filtered and concentrated to afford the title compound (870 mg), which is used in the next step without further purification.

Workup

  1. customAfter quenching
  2. customthe reaction with water
  3. customthe solvent is removed in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with brine
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-15d03c4c681e44989f868d3ab7184f0b
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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