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

HRID 1924997Notes

Reaction equation

HRID 1924997 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-42fe122bf70b4587a8a57952928c0960
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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