Hydrochloric Acid → HCID 15457056, compound

HRID 1385934Notes

Reaction equation

HRID 1385934 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[C:12](=[O:22])[N:13]([CH3:21])[C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)=[C:4]([F:23])[CH:3]=1.[Sn].Cl.O>C(O)C>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:23])=[C:5]([C:11]2[C:12](=[O:22])[N:13]([CH3:21])[C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5352426Tin atomHCID 15457055HCID 15457055, compound

Product 1

HCID 15457056HCID 15457056, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g (2.8 mmol) of 3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone and 1.3 g (11 mmol) of tin were suspended in 30 ml of ethanol, and 5 ml of concentrated hydrochloric acid was added at room temperature, followed by stirring for 1 hour. After completion of the reaction, the reaction solution was poured into water and neutralized. Insoluble substances were filtered off, and the filtrate was extracted with ethyl acetate. After washing with water and a saturated sodium hydrogencarbonate aqueous solution, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. Then, the obtained crude crystals were washed with diisopropyl ether to obtain 0.90 g (yield: 98%) of the desired product. Melting point: 155-157° C.

Workup

  1. customAfter completion of the reaction
  2. filtrationInsoluble substances were filtered off
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washAfter washing with water
  5. dry with materiala saturated sodium hydrogencarbonate aqueous solution, the organic layer was dried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customThen, the obtained crude crystals
  8. washwere washed with diisopropyl ether

Sources & evidence

ORD record
ord-303e1865cbd340b187412aebf81afe5c
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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