Nitroethane → Amphetamine

HRID 257312Notes

Reaction equation

HRID 257312 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-])=O.[N+:12]([CH2:15][CH3:16])([O-])=O.C([O-])(=O)C.[NH4+].CCCCCC.C(OCC)(=O)C>C(O)(=O)C>[NH2:12][CH:15]([CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[CH:4][CH:5]=1)[CH3:16]

Participants

6

Reactant 4

HCID 6587NitroethaneHCID 74493-NitrobenzaldehydeHCID 517165Ammonium AcetateHCID 21226206Ethyl acetate hexane

Product 1

HCID 3007AmphetamineYield 32%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 7.56 g (50 mmol) of 3-nitrobenzaldehyde, 11.25 g (150 mmol) of nitroethane and 4.24 g (55 mmol) of ammonium acetate was heated in 2 mL of acetic acid in a 110° C. oil bath for 2 1/2 hours. Subsequent examination of the mixture by preparative thin layer chromatography with hexane/ethyl acetate showed almost no starting material remaining. Volatile materials were removed with a rotary evaporator, and the residue was partitioned between dichloromethane and water, with washing of the organic layer twice with 10% sodium bicarbonate. Caution was necessary because gas evolution occurred during the first bicarbonate wash. Drying was performed with magnesium sulfate. Filtration and removal of solvent left 9.13 g of crude product. Half of this was chromatographed on a 3×35 cm flash silica column, packed with hexane and eluted with 7:1 hexane/ethyl acetate to give 1.66 g (32%) of pure title compound.

Workup

  1. customVolatile materials were removed with a rotary evaporator
  2. customthe residue was partitioned between dichloromethane and water
  3. washwith washing of the organic layer twice with 10% sodium bicarbonate
  4. washwash
  5. customDrying
  6. filtrationFiltration and removal of solvent
  7. waitleft 9.13 g of crude product
  8. customHalf of this was chromatographed on a 3×35 cm flash silica column
  9. washeluted with 7:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-51d6fa439c3845dbaa4f21f86008b6dc
Source dataset
uspto-grants-1993_11
Patent number
US05262333

Reaction notes

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