Hydrochloric Acid → 3-(4-nitrophenyl)-2-hydroxy-N-(2-aminoethyl)propionamide

HRID 377013

Reaction equation

HRID 377013 reaction equation
C1([C:7]([CH3:12])([OH:11])[C:8]([OH:10])=O)C=CC=CC=1.[N+]([O-])(O)=O.Cl.C(O[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:25]=1C)(=O)C(C)O.[CH2:34]([NH2:37])[CH2:35][NH2:36]>S(=O)(=O)(O)O.CO>[N+:30]([C:27]1[CH:26]=[CH:25][C:24]([CH2:12][CH:7]([OH:11])[C:8]([NH:36][CH2:35][CH2:34][NH2:37])=[O:10])=[CH:29][CH:28]=1)([O-:32])=[O:31]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 1303Atrolactic acidHCID 3301EthylenediamineHCID 56998982Methyl-p-nitrophenyl lactate

Product 1

HCID 193607333-(4-nitrophenyl)-2-hydroxy-N-(2-aminoethyl)propionamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

Phenyl-lactic acid (available from Aldrich Chemical Co., Milwaukee, Wis.) is nitrated with nitric acid in sulfuric acid. P-nitrophenyl lactic acid is esterified with methanol and gaseous hydrochloric acid. Methyl-p-nitrophenyl lactate is condensed with ethylene diamine to provide the amide adduct, 3-(4-nitrophenyl)-2-hydroxy-N-(2-aminoethyl)propionamide.

Sources & evidence

ORD record
ord-1457048d56e0407caf57f36a180c5d16
Source dataset
uspto-grants-2000_02
Patent number
US06022966

Linked notes

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