Ammonia → 3-Nitrobenzylamine

HRID 2276980Notes

Reaction equation

HRID 2276980 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].[NH3:12]>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][NH2:12])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 1227223-NitrobenzylamineYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-Nitrobenzyl bromide (10 g, 46.3 mmol) was dissolved in ethanol (200 ml) and stirred at room temperature A solution of conc.NH3 (aq) (200 ml) in ethanol (300 ml) was added dropwise to the reaction over 30 minutes. The reaction was stirred for 18 h at room temperature before evaporating to dryness. Water (350 ml) was added to the residue and the solution was washed with EtOAc (2×200 ml). The aqueous layer was basified with 1M NaOH and extracted with EtOAc (2×200 ml). The organic extracts of the basic layer were combined, dried (Na2SO4) and evaporated to dryness. The product was obtained as an orange oil (4.6 g, 65% yield). LCMS purity 100%, m/z 153 [M++H]+.

Workup

  1. stirringThe reaction was stirred for 18 h at room temperature
  2. custombefore evaporating to dryness
  3. additionWater (350 ml) was added to the residue
  4. washthe solution was washed with EtOAc (2×200 ml)
  5. extractionextracted with EtOAc (2×200 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-f2226950534043fa9e315d9f451d79c3
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

Loading…