Sodium Hydroxide → N-Butyl beta-carboline-3-carboxylate

HRID 1619473Notes

Reaction equation

HRID 1619473 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([OH:16])=[O:15])[N:2]=1.[OH-].[Na+].S(Cl)(Cl)=O>C(O)CCC>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16][CH2:14][CH2:3][CH2:4][CH3:5])=[O:15])[N:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 1732629H-Pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 128618N-Butyl beta-carboline-3-carboxylateYield 134.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Compound 17 (2.1 g, 10 mmol), NaOH (0.8 g, 20 mmol), n-butanol (100 ml) and thionyl chloride (5 ml) were added into a 250 ml round-bottom flask. The mixture was refluxed for 6 h. Excessive n-butanol was then removed in reduced pressure. The residues were dissolved in water followed by the addition of ethyl acetate. While being stirred, the mixture was adjusted to pH 8 with NaHCO3 solution. The organic layer was isolated. The aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with water and brine, dried over anhydrous sodium sulfate, decolorized with activated carbon and concentrated in vacuum. The residues were dissolved in ethyl acetate, and purified by silica gel column chromatography with ethyl acetate as the eluent, the recrystallized with ethyl ether/petroleum ether (2:5) to afford white needle crystals (1.8 g, 67%), and mp 211-212° C. (reference [1]: 210-211° C.).

Workup

  1. temperatureThe mixture was refluxed for 6 h
  2. customExcessive n-butanol was then removed in reduced pressure
  3. dissolutionThe residues were dissolved in water
  4. additionfollowed by the addition of ethyl acetate
  5. customThe organic layer was isolated
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. washwashed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuum
  10. dissolutionThe residues were dissolved in ethyl acetate
  11. custompurified by silica gel column chromatography with ethyl acetate as the eluent
  12. customthe recrystallized with ethyl ether/petroleum ether (2:5)

Sources & evidence

ORD record
ord-076d8f7421bc4d79baf7d6c0c7ee167b
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

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