Dimethylformamide → 9H-pyrido[3,4-b]indole-3-carboxaldehyde oxime

HRID 1982445Notes

Reaction equation

HRID 1982445 reaction equation
[OH-].[K+].CN(C)C=O.[CH:8]1[C:20]2[NH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[C:10]([CH:21]=O)[N:9]=1.[OH:23][NH:24]Cl>CO>[CH:8]1[C:20]2[NH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[C:10]([CH:21]=[N:24][OH:23])[N:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 149953Hydroxylamine, N-chloro-HCID 127891449H-pyrido[3,4-b]indole-3-carbaldehyde

Product 1

HCID 1363992769H-pyrido[3,4-b]indole-3-carboxaldehyde oximeYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.1 g of potassium hydroxide in 40 ml of methanol is added to a mixture of 150 ml of dimethylformamide, 6.9 g of beta-carboline-3-carboxaldehyde and 3.1 g of hydroxylamino-hydrochloride. The reaction mixture is allowed to stand at room temperature overnight. After evaporation, 50 ml of water is added. The reaction product is filtered off. 6.9 g of the air-dried product is heated in the steam bath together with 35 ml of 2 propanol and, after cooling, is filtered off. 5 g of beta-carboline-3-carboxaldehyde-oxime with a melting point of 229°-231° C. is obtained.

Workup

  1. customAfter evaporation, 50 ml of water
  2. additionis added
  3. filtrationThe reaction product is filtered off
  4. temperature6.9 g of the air-dried product is heated in the steam bath together with 35 ml of 2 propanol
  5. temperatureafter cooling
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-62a6d00a5fcc4bfdba927214b19cc2bf
Source dataset
uspto-grants-1986_06
Patent number
US04596808

Reaction notes

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