Hydrochloric Acid → HCID 18408328, compound

HRID 1385964Notes

Reaction equation

HRID 1385964 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:11](OCC)=[O:12])[CH3:10])[C:5]([N+:16]([O-])=O)=[CH:4][C:3]=1[C:19]1[C:20](=[O:30])[N:21]([CH3:29])[C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=1.[Sn].Cl>C(O)C>[Cl:1][C:2]1[C:3]([C:19]2[C:20](=[O:30])[N:21]([CH3:29])[C:22]([C:25]([F:26])([F:28])[F:27])=[CH:23][CH:24]=2)=[CH:4][C:5]2[NH:16][C:11](=[O:12])[CH:9]([CH3:10])[O:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 18408340HCID 18408340, compound

Product 1

HCID 18408328HCID 18408328, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 10 ml of ethanol, 0.90 g (2.0 mmol) of 3-[2-chloro-4-(1-ethoxycarbonylethoxy)-5-nitrophenyl]-1-methyl-6-trifluoromethyl-2(1H)-pyridone and 1 g (8.5 mmol) of tin were added, and 2 ml of concentrated hydrochloric acid was added thereto with stirring at room temperature, followed by stirring for 1 hour. After completion of the reaction, excess ethanol was distilled off under reduced pressure, 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 0.7 g (yield: 91%) of the desired product. 1H-NMR (300 MHz, CDCl3) δ value: 1.63(3H,d), 3.70(3H,d), 4.67(1H,q), 6.77(1H,d), 6.83(1H,s), 7.08(1H,s), 7.35(1H,d,J=7.80)ppm.

Workup

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

Sources & evidence

ORD record
ord-d02ac99233fb4f67a4e9b7b4a3150e4d
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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