Ethanol → 9H-Pyrido(3,4-b)indole-3-carboxylic acid

HRID 1619472Notes

Reaction equation

HRID 1619472 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]([O:16]CC)=[O:15])[N:2]=1.[OH-].[Na+].C(O)C>O>[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

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 105078Ethyl Beta-Carboline-3-Carboxylate

Product 1

HCID 1732629H-Pyrido(3,4-b)indole-3-carboxylic acidYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 10 (1.2 g, 5 mmol), NaOH (0.8 g, 20 mmol), ethanol (20 ml) and H2O (40 ml) were added into a 50 ml round-bottom flask. The mixture was refluxed for 2 h. Ethanol was then evaporated in reduced pressure. The mixture was adjusted to pH with 5M HCl. After cooling with cold water, filtration, wash well with water and recrystallization with ethanol, white solids (0.96 g, 90%) were obtained. and mp 307-309° C. (reference[1]: 310° C.).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customEthanol was then evaporated in reduced pressure
  3. temperatureAfter cooling with cold water, filtration
  4. washwash well with water and recrystallization with ethanol

Sources & evidence

ORD record
ord-5235da5f8c1549359ef7492f9ff2b659
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

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