5-Morpholino-2-nitrobenzaldehyde → (5-Morpholin-4-YL-2-nitro-phenyl)-methanol

HRID 1487194Notes

Reaction equation

HRID 1487194 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[C:11]([CH:14]=2)[CH:12]=[O:13])[CH2:3][CH2:2]1.[BH4-].[Na+]>O1CCCC1.C(O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[C:11]([CH2:12][OH:13])[CH:14]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 37709635-Morpholino-2-nitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 9878047(5-Morpholin-4-YL-2-nitro-phenyl)-methanolYield 62.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the crude 5-morpholino-2-nitrobenzaldehyde in a mixture of tetrahydrofuran and ethanol (100 mL/100 mL) was slowly added sodium borohydride (4.0 g). The mixture was stirred at room temperature for 1 hour, and then was partitioned between ether and saturated ammonium chloride. The aqueous phase was extracted with ether, and the organic phases were combined, washed by brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product (5-morpholino-2-nitrophenyl)methanol (8.5 g, yield 62.3%, two steps).

Workup

  1. customwas partitioned between ether and saturated ammonium chloride
  2. extractionThe aqueous phase was extracted with ether
  3. washwashed by brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-d360d0afff0a4b4eb45936de0ac05813
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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