Hydrochloric Acid → HCID 15457077, compound

HRID 1385960Notes

Reaction equation

HRID 1385960 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[C:12]1[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=1.[Sn].Cl>C(O)C>[NH2:9][C:5]1[C:6]([OH:8])=[CH:7][C:2]([Cl:1])=[C:3]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 15457076HCID 15457076, compound

Product 1

HCID 15457077HCID 15457077, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

8.0 g (23 mmol) of 3-(2-chloro-4-hydroxy-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone and 8.2 g (69 mmol) of tin were added to 100 ml of ethanol, and 5 ml of concentrated hydrochloric acid was added thereto under stirring at room temperature, followed by stirring for 1 hour. After completion of the reaction, excess ethanol was distilled off, and the residue was neutralized with a saturated sodium hydrogencarbonate aqueous solution and then extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure to obtain 6.5 g (yield: 90%) of the desired product. 1H-NMR (300 MHz, CDCl3) δ value: 3.74(3H,s), 6.83(1H,d), 7.23(1H,d), 7.30(1H,d), 7.57(1H,d)ppm.

Workup

  1. additionwas added
  2. stirringby stirring for 1 hour
  3. distillationwas distilled off
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe organic layer was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8be61c11e1354dc2a9263d423326f964
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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