Acetone → HCID 13136249, compound

HRID 1903117Notes

Reaction equation

HRID 1903117 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([C:19]#[C:20][CH2:21][OH:22])=[CH:13][CH:12]=3)=[O:5])[CH3:2].CC(C)=O>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([C:19]#[C:20][CH:21]=[O:22])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 180AcetoneHCID 13136246HCID 13136246, compound

Product 1

HCID 13136249HCID 13136249, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst3×HCID 6212ChloroformSolvent

Procedure

300 mg of 6-(3-hydroxy-1-propinyl)-beta-carboline-3-carboxylic-acid-ethylester is suspended in 25 ml of chloroform and 25 ml of acetone and mixed with 1.4 g of manganese dioxide. After stirring for 4 h, manganese dioxide is added again in an amount of 0.4 g. After standing overnight, 0.4 g of manganese dioxide is added again and the mixture is stirred for 8 h. Then it is filtered and the manganese dioxide is extracted in an Soxhlet extractor under acetone. After consolidating the filtrates, 150 mg of 6-(3-oxo-1-propinyl)-beta-carboline-3-carboxylic-acid-ethylester is obtained.

Workup

  1. waitAfter standing overnight
  2. stirringthe mixture is stirred for 8 h
  3. filtrationThen it is filtered
  4. extractionthe manganese dioxide is extracted in an Soxhlet extractor under acetone

Sources & evidence

ORD record
ord-46af6116c66a4cf6ab015f45147ab5b5
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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