Nitric Acid → HCID 1501934, compound

HRID 1768745Notes

Reaction equation

HRID 1768745 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.[N+:12]([O-])([OH:14])=[O:13].[OH-].[Na+]>S(=O)(=O)(O)O.O>[NH2:11][C@@H:7]([C:4]1[CH:3]=[CH:2][CH:1]=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1)[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 99291L-Phenylglycine

Product 1

HCID 1501934HCID 1501934, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of L-phenylglycine (10 g) in 40 mL of conc. sulfuric acid was cooled in an ice water/acetone bath. 90% Nitric acid (3.72 mL) was added dropwise over a 30 minute period at such a rate as to keep the internal temperature below 10° C. After addition was complete, stirring was continued for 1 hour at 0° C. and then the reaction mixture was allowed to warm to room temperature over 1.5 hours. The reaction mixture was poured onto 200 g of crushed ice and the resulting mixture was neutralized with sodium hydroxide to pH 7. The reaction mixture was diluted with 600 mL of water, Celite was added and the resulting suspension was filtered and concentrated to give the crude product D contaminated with sodium sulfate. This material was taken to the next step without further purification.

Workup

  1. customthe internal temperature below 10° C
  2. additionAfter addition
  3. additionwas added
  4. filtrationthe resulting suspension was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5e34729f057f4f7e8ca6b909de18b4dc
Source dataset
uspto-grants-1995_01
Patent number
US05378838

Reaction notes

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