Ethanol → HCID 86712399, compound

HRID 2174194Notes

Reaction equation

HRID 2174194 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([O:17][C:18]1[C:19]([C:24]([CH3:28])([CH3:27])[C:25]#N)=[N:20][CH:21]=[CH:22][CH:23]=1)=[CH:12]2.C(=O)([O-])[OH:30].[Na+].[CH2:34]([OH:36])[CH3:35]>>[CH2:34]([O:36][C:25](=[O:30])[C:24]([C:19]1[C:18]([O:17][C:13]2[CH:14]=[N:15][C:16]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][C:7]=3[F:6])=[CH:23][CH:22]=[CH:21][N:20]=1)([CH3:27])[CH3:28])[CH3:35]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86712397HCID 86712397, compound

Product 1

HCID 86712399HCID 86712399, compound

Conditions

Temperature
100 °C

Procedure

2 ml of ethanol and 2 ml of concentrated sulfuric acid were added to 0.38 g of 2-[3-(8-fluoro-quinolin-3-yloxy)-pyridin-2-yl]-2-methylpropionitrile. The mixture was stirred for 6 hours at 100° C. Subsequently, saturated aqueous sodium hydrogen carbonate solution was added thereto to stop the reaction. The resultant was then extracted with ethyl acetate followed by distilling off the solvent of the organic layer. Subsequently, the resultant was purified by silica gel column chromatography to obtain 0.24 g of 2-[3-(8-fluoro-quinolin-3-yloxy)-pyridin-2-yl]-2-methylpropionic acid ethyl ester.

Workup

  1. customthe reaction
  2. extractionThe resultant was then extracted with ethyl acetate
  3. distillationby distilling off the solvent of the organic layer
  4. customSubsequently, the resultant was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d1ec422ddc324f2890c3a152f514fa1b
Source dataset
uspto-grants-2015_06
Patent number
US09060517B2

Reaction notes

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