3-Hydroxymethyl-beta-carboline → 9H-pyrido[3,4-b]indole-3-carbaldehyde

HRID 1903102Notes

Reaction equation

HRID 1903102 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>O>[CH:5]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:15]=[C:3]([CH:2]=[O:1])[N:4]=1

Participants

4

Reactant 2

HCID 53533383-Hydroxymethyl-beta-carbolineHCID 178418268HCID 178418268, compound

Product 1

HCID 127891449H-pyrido[3,4-b]indole-3-carbaldehydeYield 82.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.3 g of 3-hydroxymethyl-beta-carboline, 300 ml of water-free pyridine and 9.9 g of lead tetra-acetate is heated in an oil bath for 4 h at about 80° C. After cooling and evaporation, 150 ml of water is added. The crystalline residue is filtered off, washed with a 5% aqueous potassium carbonate solution and then again with water. The air-dried product (3.5 g) is boiled in 0.7 liters of 2-propanol with activated carbon and is filtered hot. After evaporation, 2.7 g of beta-carboline-3-carboxaldehyde is obtained, with a melting point of 270° C. (decomposition).

Workup

  1. temperatureAfter cooling
  2. customevaporation, 150 ml of water
  3. additionis added
  4. filtrationThe crystalline residue is filtered off
  5. washwashed with a 5% aqueous potassium carbonate solution
  6. filtrationis filtered hot
  7. customAfter evaporation

Sources & evidence

ORD record
ord-07c29d57aa4c4b39b2e0223143820cc5
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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