N-[(4-Fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl ester → N-[(3-Amino-4-fluorophenyl)-carbamoyl]glycine, ethyl ester

HRID 363167

Reaction equation

HRID 363167 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])=[CH:4][C:3]=1[N+:18]([O-])=O.[H][H]>[Pt].C(OCC)(=O)C>[NH2:18][C:3]1[CH:4]=[C:5]([NH:8][C:9]([NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 85708209N-[(4-Fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 85708212N-[(3-Amino-4-fluorophenyl)-carbamoyl]glycine, ethyl esterYield 60.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[(4-fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl ester (8 g, 0.029 mol) and 5% platinum on activated carbon (0.5 g) in ethyl acetate is hydrogenated at 50 psi until hydrogen uptake is complete. The reaction mixture is then filtered and cooled in an ice-bath until a solid forms. The solid is collected by filtration and air-dried to give the title product as a white solid (4.5 g, mp 152°-153° C.).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. temperaturecooled in an ice-bath until a solid forms
  3. filtrationThe solid is collected by filtration
  4. customair-dried

Sources & evidence

ORD record
ord-a8d5ec738d0b474e8901afb316d95be4
Source dataset
uspto-grants-1999_02
Patent number
US05872253

Linked notes

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