Hydrochloric Acid → 2-(3-Nitrophenyl)ethan-1-amine

HRID 1518180Notes

Reaction equation

HRID 1518180 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CSC.B.Cl>C1COCC1.C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][NH2:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 121253-NitrophenylacetonitrileHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 129500662-(3-Nitrophenyl)ethan-1-amineYield 112%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3-nitro-phenyl)-acetonitrile (11.4 g, 70.4 mmol) in THF (100 ml) was heated to reflux and borane dimethylsulfide (2M in THF, 77.34 mmol) was added. The mixture was stirred for 2 h under reflux. After complete conversion the mixture was allowed to come to room temperature and a solution of HCl in ethanol (1M) was added. After stirring the mixture for 30 min it was concentrated under reduced pressure. The residue was triturated with diethylether, filtered, washed with diethylether and dried in vacuo to give the product as a yellow powder (13.1 g, 92%).

Workup

  1. temperatureto reflux
  2. temperatureunder reflux
  3. customto come to room temperature
  4. stirringAfter stirring the mixture for 30 min it
  5. concentrationwas concentrated under reduced pressure
  6. customThe residue was triturated with diethylether
  7. filtrationfiltered
  8. washwashed with diethylether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-5039f9c7ef74498ca54e64ca1fa1530d
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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