2-[(2-methoxy-4-methylmercapto-benzoyl)-amino]-3-nitro-1H-pyridin-6-one → HCID 178418498, compound

HRID 3855Notes

Reaction equation

HRID 3855 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([S:22][CH3:23])[CH:19]=[CH:18][C:4]=1[C:5]([NH:7][C:8]1[NH:9][C:10](=[O:17])[CH:11]=[CH:12][C:13]=1[N+:14]([O-])=O)=O>C(O)(=O)C.[H][H].[Pd]>[CH3:1][O:2][C:3]1[CH:21]=[C:20]([S:22][CH3:23])[CH:19]=[CH:18][C:4]=1[C:5]1[N:7]=[C:8]2[NH:9][C:10](=[O:17])[CH2:11][CH:12]=[C:13]2[N:14]=1

Participants

5

Reactant 1

HCID 544512662-[(2-methoxy-4-methylmercapto-benzoyl)-amino]-3-nitro-1H-pyridin-6-one

Product 1

HCID 178418498HCID 178418498, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

An amount of 6.2 gm of 2-[(2-methoxy-4-methylmercapto-benzoyl)-amino]-3-nitro-1H-pyridin-6-one is dissolved in 370 ml of glacial acetic acid and hydrogenated with hydrogen in the presence of 6 gm of 10% palladium charcoal at ambient temperature under 5 bars of pressure (duration of reaction: two hours). The catalyst is filtered off, and the filtrate is refluxed for about 1.5 hours with stirring. Then, about 250 ml of the solvent is evaporated off, and the remaining solution is poured onto ice water and neutralized with ammonia. The precipitate obtained is recrystallized from methanol. Another fraction can be obtained by evaporating the mother liquors of crystallization and triturating the residue with ether:

Workup

  1. filtrationThe catalyst is filtered off
  2. temperaturethe filtrate is refluxed for about 1.5 hours
  3. customThen, about 250 ml of the solvent is evaporated off
  4. additionthe remaining solution is poured onto ice water and neutralized with ammonia
  5. customThe precipitate obtained
  6. customis recrystallized from methanol
  7. customAnother fraction can be obtained
  8. customby evaporating
  9. customthe mother liquors of crystallization
  10. customtriturating the residue with ether

Sources & evidence

ORD record
ord-635cfe2f33674766827bc3eaf4c9f1ef
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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