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

HRID 280038Notes

Reaction equation

HRID 280038 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].Cl>S(=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 3

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 6140L-Phenylalanine

Product 1

HCID 137064-Nitro-3-phenyl-L-alanineYield 43%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Using the procedure of Bergel and Stock as set forth in J. Chem. Soc., 2409-2417 (1954) L-phenylalanine (50 g) was treated with a mixture of concentrated sulfuric acid (150 ml), and fuming nitric acid (28 ml) to produce the nitro compound Yield 26.9 g (43%) mp 232°-234° C., [α]D25 =+9.6° (c=1.77, 1N HCl).

Sources & evidence

ORD record
ord-bcffd1e26f1f46a8acd5510ab76f2131
Source dataset
uspto-grants-1986_05
Patent number
US04587046

Reaction notes

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