1-(2-Chloro-4-fluoro-5-nitrophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione → 1-(5-Amino-2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione

HRID 52410

Reaction equation

HRID 52410 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[N:12]1[C:17](=[O:18])[NH:16][C:15](=[O:19])[N:14]([CH3:20])[C:13]1=[O:21].[H][H]>[Pt].C(OCC)(=O)C>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Cl:1])=[C:3]([N:12]2[C:17](=[O:18])[NH:16][C:15](=[O:19])[N:14]([CH3:20])[C:13]2=[O:21])[CH:4]=1

Participants

5

Reactant 2

HCID 572803321-(2-Chloro-4-fluoro-5-nitrophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trioneHCID 178418361HCID 178418361, compound

Product 1

HCID 109350601-(5-Amino-2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-chloro-4-fluoro-5-nitrophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (28.5 g, 0.09 mol) and 5% platinum on activated carbon (1 g) in ethyl acetate is hydrogenated at 55 psi until hydrogen uptake is complete. The reaction mixture is then filtered and concentrated in vacuo to give the title product as a white solid, mp 244°-245° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f01dc30df53843838603cbb2252ed02f
Source dataset
uspto-grants-1997_04
Patent number
US05616706

Linked notes

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