HCID 13432877, compound → HCID 13432847, compound

HRID 1197866Notes

Reaction equation

HRID 1197866 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:6]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)=[N:5][N:4]=1)[CH3:2]>[Pt]=O.Cl>[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:6]([C:16]2[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)=[N:5][N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 13432877HCID 13432877, compound

Product 1

HCID 13432847HCID 13432847, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 313Hydrochloric AcidSolvent

Procedure

100 g of the product of Example 1 were mixed at ambient temperature with 500 ml of 2N hydrochloric acid with stirring and a partial solution and then a crystallization were obtained. 0.5 g of 0.5% platinum oxide was then added, and stirring was continued for 4 days at 35°-38° C. under an atmosphere of hydrogen. After filtering, washing with water, the mixture was made alkaline with a pH of 11 with sodium hydroxide. The mixture was stirred for 1 hour at 20°-25° C. and filtered. The product was washed with water and dried at 60° C. to obtain 90.75 g of crude product. The latter was purified by triturating at reflux in ethyl acetate to obtain 90.7 g of 4-[5-ethyl-4-(4-methoxyphenyl)-4H-1,2,4-triazole-3-yl]-benzenamine melting at 210° C.

Workup

  1. customa partial solution and then a crystallization
  2. customwere obtained
  3. stirringstirring
  4. filtrationAfter filtering
  5. washwashing with water
  6. stirringThe mixture was stirred for 1 hour at 20°-25° C.
  7. filtrationfiltered
  8. washThe product was washed with water
  9. customdried at 60° C.
  10. customto obtain 90.75 g of crude product
  11. customThe latter was purified
  12. customby triturating
  13. temperatureat reflux in ethyl acetate

Sources & evidence

ORD record
ord-abe2cd80bde24b09a6973960ec733f44
Source dataset
uspto-grants-1994_01
Patent number
US05278180

Reaction notes

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