Calcium Carbonate → 2-Nitrophenethylamine

HRID 459884Notes

Reaction equation

HRID 459884 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Ca+2].[N:25]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N+:36]([O-:38])=[O:37])=[N+]=[N-]>C1C=CC=CC=1>[NH2:25][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N+:36]([O-:38])=[O:37]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 11776TriphenylphosphineHCID 184442461-(2-Azidoethyl)-2-nitrobenzene

Product 1

HCID 124981232-Nitrophenethylamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Triphenylphosphine (31.1 g, 0.118 mol) and calcium carbonate (50 mg, 0.5 mmol) were added to a solution of 2-(2-azidoethyl)nitrobenzene (22.8 g, 0.118 mol) in benzene (500 mL). The reaction was stirred at room temperature until complete. The solvent was removed in vacuo, and the residue treated with acetic acid (100 mL) and 48% hydrogen bromide (100 mL) at 100° C. for 1 h. The reaction was cooled and concentrated. Water was added and the solution extracted with methylene chloride. The aqueous layer was made basic by the addition of 5% aqueous sodium hydroxide solution, then extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over sodium sulfate. The title compound was obtained as an oil (8.0 g). MS 167 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue treated with acetic acid (100 mL) and 48% hydrogen bromide (100 mL) at 100° C. for 1 h
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. additionWater was added
  6. extractionthe solution extracted with methylene chloride
  7. additionThe aqueous layer was made basic by the addition of 5% aqueous sodium hydroxide solution
  8. extractionextracted with ethyl acetate
  9. washThe organic phase was washed with saturated brine
  10. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-af16394fa28d465cac248f1a06bea1ec
Source dataset
uspto-grants-2007_03
Patent number
US07196079B2

Reaction notes

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