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

HRID 1466

Reaction equation

HRID 1466 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)[NH:16][C:15](=O)[N:14]([CH3:20])[C:13]1=O.[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[CH:17]=[N:16][CH2:15][N:14]([CH3:20])[CH2:13]2)[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 1317205461-(5-Amino-2-chloro-4-fluorophenyl)-3-methyl-s-triazine

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-08b8b8866d334d3cae4bec9581c21467
Source dataset
uspto-grants-1998_03
Patent number
US05726126

Linked notes

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