Borane → [2-(2-Chloro-4-nitrophenyl)ethyl]diethylamine

HRID 898551Notes

Reaction equation

HRID 898551 reaction equation
B.[Cl:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH2:12][C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=O>C1COCC1>[Cl:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH2:12][CH2:13][N:15]([CH2:16][CH3:17])[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 6331BoraneHCID 688195332-Chloro-N,N-diethyl-4-nitrobenzeneacetamide

Product 1

HCID 68816908[2-(2-Chloro-4-nitrophenyl)ethyl]diethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

65 mL (65.000 mmol) borane (1 M in THF) was added at RT to a solution of 3.702 g (13.673 mmol) 2-(2-chloro-4-nitro-phenyl)-N,N-diethyl-acetamide in 130 mL THF and the mixture was stirred for 4 h . The reaction mixture was evaporated down i. vac., the residue was combined with 15 mL MeOH and 15 mL semiconc. aqueous HCl and heated to 100° C. for 15 min. Water was added, the mixture was made basic with aqueous sodium carbonate solution and the aqueous phase was extracted with EtOAc. The combined org. phases were washed with water and saturated aqueous NaCl solution, dried over sodium sulphate and evaporated down i. vac. The crude product was purified by column chromatography (Alox, neutral, act. II-III, gradient petroleum ether/EtOAc 8:1→4:1).

Workup

  1. customThe reaction mixture was evaporated down i
  2. additionWater was added
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washphases were washed with water and saturated aqueous NaCl solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated down i
  7. customThe crude product was purified by column chromatography (Alox, neutral, act. II-III, gradient petroleum ether/EtOAc 8:1→4:1)

Sources & evidence

ORD record
ord-28ab7f35714e4aa2ba6c12246d8ae0d6
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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