Ethanol → HCID 178468540, compound

HRID 2192802Notes

Reaction equation

HRID 2192802 reaction equation
[OH:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:12])(C)[CH2:9][CH2:10][C:5]2=[CH:4][C:3]=1[C:13]([OH:15])=[O:14].S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[OH:1][C:2]1[C:3]([C:13]([O:15][CH2:21][CH3:22])=[O:14])=[CH:4][C:5]2[CH2:10][CH2:9][CH2:8][CH2:12][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 178423801HCID 178423801, compound

Product 1

HCID 178468540HCID 178468540, compound

Procedure

2-Hydroxy-7,7-dimethyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid (11.0 g) was dissolved in ethanol (100 ml), sulfuric acid (3.4 ml) was added and the mixture was stirred with heating to reflux for 12 hr. The reaction mixture was concentrated under reduced pressure to a half volume, the residue was basified with 8 M aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with 1 M aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (50:50-85:15) was concentrated under reduced pressure to give the object compound (3.45 g).

Workup

  1. temperaturewith heating
  2. temperatureto reflux for 12 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure to a half volume
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed successively with 1 M aqueous sodium hydroxide solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. washthe fraction eluted with ethyl acetate-hexane (50:50-85:15)
  9. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-c882d6ab90394c9d829172efd2b35d1f
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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