Acetic Acid → 3-(4-Nitrophenyl)propan-1-amine

HRID 1085291Notes

Reaction equation

HRID 1085291 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([NH2:14])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].C(O)(=O)C.CO>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][NH2:14])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 135960733-(4-Nitrophenyl)propanamide

Product 1

HCID 144850933-(4-Nitrophenyl)propan-1-amineYield 64.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10.0 g of the amide compound and 9.5 g of sodium borohydride were suspended in 250 ml of dioxane, followed by the dropwise addition of 15 ml of acetic acid. The resultant mixture was stirred for 10 hours under reflux. The reaction mixture was added with 10 ml of methanol and then concentrated to dryness. The residue was dissolved in chloroform. The solution thus obtained was washed with water and then concentrated to dryness, thereby obtaining 6.0 g of 3-(4-nitrophenyl)propylamine as an oily substance. This compound was provided for the next reaction without any further purification.

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in chloroform
  4. customThe solution thus obtained
  5. washwas washed with water
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-717cd8b07f83458bb5b0252cc2cc80e0
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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