Hydrochloric Acid → HCID 86639432, compound

HRID 1690216Notes

Reaction equation

HRID 1690216 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([C:12]1[CH:29]=[CH:28][C:15]([O:16][C:17]2[CH:18]=[C:19]([C:24]([I:27])=[CH:25][N:26]=2)[C:20]([O:22]C)=[O:21])=[C:14]([CH2:30][CH2:31][CH3:32])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[OH-].[Na+].Cl.C(=O)([O-])O.[Na+]>CO>[F:34][C:2]([F:1])([F:33])[C:3]([C:12]1[CH:29]=[CH:28][C:15]([O:16][C:17]2[CH:18]=[C:19]([C:24]([I:27])=[CH:25][N:26]=2)[C:20]([OH:22])=[O:21])=[C:14]([CH2:30][CH2:31][CH3:32])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 59200901HCID 59200901, compound

Product 1

HCID 86639432HCID 86639432, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-5-iodoisonicotinate (450 mg, 0.741 mmol) in methanol (3.5 mL), 3N aqueous solution of sodium hydroxide (3.5 mL) was added and the resultant mixture was stirred at room temperature for 1 hour. After completion of the reaction, 5% aqueous solution of hydrochloric acid and a saturated aqueous solution of sodium hydrogen carbonate were added, extracted with chloroform/methanol, and the organic layer was dried using sodium sulfate. After filtration, the filtrate was concentrated in vacuo, and 2-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-5-iodoisonicotinic acid (441 mg, yield >100%) was obtained as a yellow oil.

Workup

  1. extractionextracted with chloroform/methanol
  2. customthe organic layer was dried
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9b5e9ad376fc43758363dd243a953164
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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