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

HRID 977003
Notes
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Reaction equation

HRID 977003 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-phenylalamne (2.50 g) was suspended in water (25 ml) and cone. HCl (1 ml) was addded, 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-ba84df62857b43a99259d3b989f623be
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05612477

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes