HCID 15389009, compound → HCID 15406844, compound

HRID 580880Notes

Reaction equation

HRID 580880 reaction equation
CN(C)CCNC(C1C2C(=C(C)C3N(C)C4C=CC(O)=C(CCC)C=4C=3C=2)C=CN=1)=O.[CH2:32]([O:34][C:35]([C:37]1[C:53]2[C:41](=[C:42]([CH3:59])[C:43]3[N:44]([CH3:58])[C:45]4[CH:46]=[CH:47][C:48]([OH:57])=[C:49]([CH2:54][CH:55]=[CH2:56])[C:50]=4[C:51]=3[CH:52]=2)[CH:40]=[CH:39][N:38]=1)=[O:36])[CH3:33]>C(O)C.[Pd]>[CH2:32]([O:34][C:35]([C:37]1[C:53]2[C:41](=[C:42]([CH3:59])[C:43]3[N:44]([CH3:58])[C:45]4[CH:46]=[CH:47][C:48]([OH:57])=[C:49]([CH2:54][CH2:55][CH3:56])[C:50]=4[C:51]=3[CH:52]=2)[CH:40]=[CH:39][N:38]=1)=[O:36])[CH3:33]

Participants

5

Reactant 2

HCID 15389009HCID 15389009, compoundHCID 15406843HCID 15406843, compound

Product 1

HCID 15406844HCID 15406844, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-[(2-Dimethylaminoethyl)aminocarbonyl]-5,6-dimethyl-9-hydroxy-10-propyl-6H-pyrido-[4,3-b]carbazole ##STR26## 0.7 g of 1-ethoxycarbonyl-5,6-dimethyl-9-hydroxy-10-allyl-6H-pyrido[4,3-b]carbazole is hydrogenated in 200 ml of ethanol in the presence of 0.3 g of 10% palladium-on-carbon at 40° C. under a hydrogen pressure of 1.105Pa for 30 minutes. Filtration is carried out, the catalyst is washed with ethanol and the combined filtrates are concentrated to dryness. The residue is chromatographed on silica using as eluant first dichloromethane and then a dichloromethane/ethanol mixture (98/2). 0.362 g of 1-ethoxycarbonyl-5,6-dimethyl-9-hydroxy-10-propyl-6H-pyrido[4,3-b]carbazole is obtained. Yield: 51%.

Workup

  1. customfor 30 minutes
  2. filtrationFiltration
  3. washthe catalyst is washed with ethanol
  4. concentrationthe combined filtrates are concentrated to dryness
  5. customThe residue is chromatographed on silica using as eluant first dichloromethane

Sources & evidence

ORD record
ord-98b78cb07add4039ac7746e54a2ef711
Source dataset
uspto-grants-1999_07
Patent number
US05919791

Reaction notes

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