Hydrochloric Acid → Methyl 2-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-5-nitroisonicotinate

HRID 1690161

Reaction equation

HRID 1690161 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][CH2:20][CH3:21])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].C(=O)([O-])[O-].[K+].[K+].Cl[C:31]1[CH:32]=[C:33]([C:38]([N+:41]([O-:43])=[O:42])=[CH:39][N:40]=1)[C:34]([O:36][CH3:37])=[O:35].Cl>CN(C)C=O.O>[F:1][C:2]([F:22])([F:23])[C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:31]2[CH:32]=[C:33]([C:38]([N+:41]([O-:43])=[O:42])=[CH:39][N:40]=2)[C:34]([O:36][CH3:37])=[O:35])=[C:14]([CH2:19][CH2:20][CH3:21])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:6])([F:5])[F:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 45480451Methyl 2-chloro-5-nitroisonicotinateHCID 59201037HCID 59201037, compound

Product 1

HCID 59201113Methyl 2-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-5-nitroisonicotinateYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenol (1.68 g, 4.86 mmol) in N,N-dimethylformamide (30 mL), potassium carbonate (1.34 g) and methyl 2-chloro-5-nitroisonicotinate (1.58 g) were added, and the resultant mixture was stirred in an oil bath with the oil temperature at 80° C. After completion of the reaction, the reaction solution was neutralized by adding 2 mol/L of hydrochloric acid, added with water, and extracted with ethyl acetate. Subsequently, the organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified using thin-layer silica-gel column chromatography (hexane/ethyl acetate) and the title compound (1.86 g, yield 73%) was obtained as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washSubsequently, the organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-bcc702a03ad14fe68fb779b91f86e0a3
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Linked notes

Loading…