Hydrochloric Acid → HCID 21186735, compound

HRID 1384266Notes

Reaction equation

HRID 1384266 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[CH:4][C:3]=1C#N.Cl.[N+](=[CH2:18])=[N-].[C:19](=[O:22])(O)[O-:20].[Na+]>[OH-].[Na+].C(Cl)(Cl)Cl.C(O)=O.CCOCC>[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[CH:4][C:3]=1[C:19]([O:20][CH3:18])=[O:22]

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 9550Diazomethane2×HCID 516892Sodium BicarbonateHCID 21186724HCID 21186724, compound

Product 1

HCID 21186735HCID 21186735, compoundYield 86.3%

Reagents, catalysts & solvents 4

HCID 284Formic AcidSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Chloro-3-cyano-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (1.50 g, 7.26 mmol) was suspended in 5% sodium hydroxide aqueous solution (25.0 ml) and heated under reflux for 3.5 hours. The reaction solution was adjusted to pH 3 to 4 with concentrated hydrochloric acid and 5% hydrochloric acid at 0° C. and extracted with chloroform, and the thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the thus formed crude crystals were washed with ether to obtain crude carboxylic acid. The crude carboxylic acid was dissolved in chloroform (20.0 ml) to which was subsequently added dropwise ether solution of diazomethane at 0° C. until the material crude carboxylic acid disappeared. Formic acid was added dropwise to the reaction solution at 0° C. to effect decomposition of excess diazomethane, the resulting solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with methylene chloride, and then the thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1) to obtain the title compound (1.50 g, 86.3%) as white powder.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3.5 hours
  3. extractionextracted with chloroform
  4. washthe thus obtained organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe thus formed crude crystals
  8. washwere washed with ether
  9. customto obtain crude carboxylic acid
  10. extractionextracted with methylene chloride
  11. washthe thus obtained organic layer was washed with water and saturated brine in that order
  12. dry with materialdried over anhydrous sodium sulfate
  13. customAfter evaporation of the solvent under reduced pressure
  14. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1)

Sources & evidence

ORD record
ord-dd2a6a99f29b4737bb59ea0f8508a013
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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