(Dimethyl sulfide)trihydroboron → 2-methoxy-N-methyl-5-nitro-N-propylaniline

HRID 240919Notes

Reaction equation

HRID 240919 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]([CH3:17])[C:13](=O)[CH2:14][CH3:15].B.CSC>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]([CH3:17])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 59167877N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide

Product 1

HCID 591678992-methoxy-N-methyl-5-nitro-N-propylanilineYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide (3) (10.0 g 42 mmol) and borane-methyl sulfide complex (21 mL of 2.0M solution in tetrahydrofurane) in 50 mL THF were heated under reflux for 30 min, cooled and quenched by ice-water (slowly). Extraction with EtOAc and the organic layer washed with brine dried (Na2SO4), filtered and evaporated in vacuo to give (9.1 g, 96%) (2-Methoxy-5-nitro-phenyl)-methyl-propyl-amine (4) as a yellow oil.

Workup

  1. temperatureunder reflux for 30 min
  2. temperaturecooled
  3. customquenched by ice-water (slowly)
  4. extractionExtraction with EtOAc
  5. washthe organic layer washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-8ea7a6cbc8a24ae7a602d85ef770028a
Source dataset
uspto-grants-2014_02
Patent number
US08648104B2

Reaction notes

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