Ammonia → 3-Nitrobenzylamine

HRID 548238Notes

Reaction equation

HRID 548238 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. additionwas added dropwise to the reaction over 30 minutes
  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-1806e3f6cd964b07980622ad6f87ff27
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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