Nitric Acid → 4-Nitro-3-phenyl-L-alanine

HRID 1731647Notes

Reaction equation

HRID 1731647 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O.O>[N+:13]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C@@H:2]([C:10]([OH:12])=[O:11])[NH2:1])=[CH:5][CH:6]=1)([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 944Nitric Acid2×HCID 6140L-Phenylalanine

Product 1

HCID 137064-Nitro-3-phenyl-L-alanineYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

10.0 g (60.6 mmoles) of L-phenylalanine was dissolved in 16 ml concentrated H2SO4 (95-98%, D. 1.84 g/ml) at 0° C. 3.0 ml of HNO3 (90%, D. 1.5 g/ml) was added dropwise to the stirring solution keeping temperature at about 0° C. After all of the HNO3 has been added, the solution was allowed to stir 10-15 minutes. Reaction solution was then poured over about 200 ml of ice and then diluted to about 700 ml with additional H2O. This solution was then heated to a boil, and neutralized with PbCO3, about 80 g. The resulting precipitate was filtered and the supernatant was treated with H2S(g) to precipitate remaining Pb++, and then filtered. The resulting filtrate was reduced to 1/3 its volume. The solid which formed was filtered and washed with 95% ethanol. Yield was 50-55% of p-nitrophenylalanine when recrystallized from boiling H2O.

Workup

  1. customat about 0° C
  2. customReaction solution
  3. temperatureThis solution was then heated to a boil
  4. filtrationThe resulting precipitate was filtered
  5. additionthe supernatant was treated with H2S(g)
  6. customto precipitate
  7. filtrationfiltered
  8. customThe solid which formed
  9. filtrationwas filtered
  10. washwashed with 95% ethanol

Sources & evidence

ORD record
ord-b9abbb46cf824768b7f5a69c1e7b4651
Source dataset
uspto-grants-1986_11
Patent number
US04622420

Reaction notes

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