Hydrochloric Acid → HCID 54454612, compound

HRID 1284896Notes

Reaction equation

HRID 1284896 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([C:19]([O:21]CC4C=CC=CC=4)=[O:20])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2].CO.Cl>CN1CCCC1=O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([C:19]([OH:21])=[O:20])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13321950HCID 13321950, compound

Product 1

HCID 54454612HCID 54454612, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

At room temperature, 1.18 g of 8-benzyloxycarbonyl-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester (Example 17) is hydrogenated under a hydrogen pressure of one bar for 2 hours in a mixture of 60 ml of N-methylpyrrolidone, 20 ml of methanol, and 10 ml of 1N hydrochloric acid with 498 mg of palladium on carbon (10%). After vacuum-filtering over kieselguhr, the mixture is concentrated. The residue is extracted in a mixture of ethyl acetate, ethanol, and petroleum ether, thus obtaining 900 mg of 8-hydroxycarbonyl-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester in the form of a hydrochloride.

Workup

  1. customAt room temperature
  2. customfor 2 hours
  3. filtrationAfter vacuum-filtering over kieselguhr
  4. concentrationthe mixture is concentrated
  5. extractionThe residue is extracted in a mixture of ethyl acetate, ethanol, and petroleum ether

Sources & evidence

ORD record
ord-0ee04d8b0c00477da7af71adf2f0869a
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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