Hydrochloric Acid → N-nitro-N-methyl-L-phenylalanine

HRID 1452100Notes

Reaction equation

HRID 1452100 reaction equation
[CH3:1][NH:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.[N:15]([O-:17])=[O:16].[Na+]>O>[N+:15]([N:2]([CH3:1])[C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6951135N-MethylphenylalanineHCID 23668193Sodium Nitrite

Product 1

HCID 54111718N-nitro-N-methyl-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

N-Methyl-L-phenylalanine (2.50 g) was suspended in water (25 ml) and conc. HCl (1 ml) was added, with stirring. The solution was cooled to 5° C. and solid sodium nitrite (1.35 g) was added to the stirred solution. After stirring at 5° C. for 1 h, the reaction mixture was partitioned between dichloromethane and water. The organic solution was washed with brine and dried (MgSO4). After filtration the solvent was evaporated to yield N-nitro-N-methyl-L-phenylalanine as a white solid.

Workup

  1. stirringAfter stirring at 5° C. for 1 h
  2. customthe reaction mixture was partitioned between dichloromethane and water
  3. washThe organic solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationAfter filtration the solvent
  6. customwas evaporated

Sources & evidence

ORD record
ord-a6bf88112cd6473090692a8e66c17c5a
Source dataset
uspto-grants-1997_02
Patent number
US05606051

Reaction notes

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