N-Phenylglycine ethyl ester → HCID 46838975, compound

HRID 1664494Notes

Reaction equation

HRID 1664494 reaction equation
[N:1]([O-:3])=O.[Na+].[C:5]1([NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.Cl>[N:1]([N:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3]

Participants

5

Reactant 2

HCID 75190N-Phenylglycine ethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 46838975HCID 46838975, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of NaNO2 (9.5 g, 0.14 mol) in H2O (27 ml) is added to an ice-cold stirred solution of ethyl phenylamino-acetate (25 g, 0.14 mol) in conc. HCl (20 ml) and H2O (27 ml) within 2 h. The reaction mixture is kept stirring for 1 h and then extracted twice with CH2Cl2. The combined organic layers are washed with H2O and brine, dried over Na2SO4 and filtered. The solvent is evaporated and the crude subtitle compound thus obtained as orange oil is used without further purification. tR (LC-4) 1.02 min.

Workup

  1. extractionextracted twice with CH2Cl2
  2. washThe combined organic layers are washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-587d50b544504422a891f7251bfff6d2
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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