Ethanol → Ethyl 3,4-dihydropyrrolo[3,4-b]indole-2(1H)-carboxylate

HRID 597543Notes

Reaction equation

HRID 597543 reaction equation
C1(N[N:8]=[C:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10]2)C=CC=CC=1.P(=O)(O)(O)O.S(=O)(=O)(O)O.[CH2:29](O)[CH3:30]>[Cl-].[Zn+2].[Cl-]>[C:14]([N:11]1[CH2:12][C:13]2[C:30]3[CH:29]=[CH:12][CH:13]=[CH:9][C:10]=3[NH:8][C:9]=2[CH2:10]1)([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 85895332HCID 85895332, compound

Product 1

HCID 12371818Ethyl 3,4-dihydropyrrolo[3,4-b]indole-2(1H)-carboxylate

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

When N-carbethoxy-3-pyrrolidinone phenylhydrazone was reacted in refluxing ethanol in the presence of various strong acid catalysts such as 85% phosphoric acid, concentrated sulfuric acid and anhydrous zinc chloride, the best yield of 2-carbethoxy- 1,2,3,4-tetrahydropyrrolo[3,4-b]indole obtained was 10% of theory. The above phenylhydrazone (M.P. 138° C.) was obtained by reacting equimolar amounts of phenylhydrazine hydrochloride and N-carbethoxypyrrolidinone in refluxing ethanol. The phenylhydrazone is isolated by neutralizing the cooled reaction mixture with potassium carbonate, diluting with water, filtering and drying.

Sources & evidence

ORD record
ord-ea32af7e787e4f2693e775472026b873
Source dataset
uspto-grants-1977_03
Patent number
US04014890

Reaction notes

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