Nitric Acid → 4-amino-3-nitrophenylPropanoic acid

HRID 1626838Notes

Reaction equation

HRID 1626838 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14].O>CC(O)=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:6][C:7]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 430264-Aminohydratropic acid

Product 1

HCID 122268174-amino-3-nitrophenylPropanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(4-Aminophenyl)propanoic acid (8.45 g, 51.2 mmol) in AcOH (70 mL) was added HNO3 (60%, 5.66 g) at room temperature. The reaction mixture was refluxed for 4 hrs then cooled to room temperature. The mixture was poured into iced water (200 mL), and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hrs
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c11c442db954fa3a768db81609a8448
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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