1,1-Dimethylhydrazine → beta-Carboline-3-carboxaldehyde-dimethylhydrazone

HRID 1903105Notes

Reaction equation

HRID 1903105 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]([CH:14]=O)[N:2]=1.CN(C)C=O.[CH3:21][N:22]([CH3:24])[NH2:23]>O>[CH3:21][N:22]([CH3:24])[N:23]=[CH:14][C:3]1[N:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 6228DimethylformamideHCID 127891449H-pyrido[3,4-b]indole-3-carbaldehyde

Product 1

HCID 54038756beta-Carboline-3-carboxaldehyde-dimethylhydrazone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.0 g of beta-carboline-3-carboxaldehyde, 10 ml of dimethyl-formamide and 3 ml of N,N-dimethyl hydrazine is introduced into a glass autoclave. The air is replaced by nitrogen. After stirring for 3 h, the reaction mixture is allowed to stand overnight at room temperature. After adding 25 ml of water, the reaction mixture is extracted with 100 and 50 ml of chloroform. The chloroform phase is dried using magnesium sulfate, then filtered. Then, the chloroform is evaporated. After adding 10 ml of ether, the reaction product is filtered off. 0.9 g of beta-carboline-3-carboxaldehyde-dimethylhydrazone with a m.p. of 203°-206° C. is obtained.

Workup

  1. additionis introduced into a glass autoclave
  2. waitto stand overnight at room temperature
  3. extractionthe reaction mixture is extracted with 100 and 50 ml of chloroform
  4. dry with materialThe chloroform phase is dried
  5. filtrationfiltered
  6. customThen, the chloroform is evaporated
  7. additionAfter adding 10 ml of ether
  8. filtrationthe reaction product is filtered off

Sources & evidence

ORD record
ord-a54e78f27e924fc5a7b3f6261aa42bee
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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