Indole → 7-Ethyl-1,1a,2,3,8,8b-hexahydrocyclopropa[a]-carbazole-8b-acetic Acid

HRID 2351373Notes

Reaction equation

HRID 2351373 reaction equation
C([O:3][C:4](=[O:14])[CH2:5][C:6]12[CH2:12][CH:11]1[CH2:10][CH2:9][CH2:8][C:7]2=O)C.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1.C(C1C=CC=CC=1NN)C>>[CH2:17]([C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:23]=1[NH:15][C:7]1[C:6]3([CH2:5][C:4]([OH:3])=[O:14])[CH2:12][CH:11]3[CH2:10][CH2:9][C:8]2=1)[CH3:16]

Participants

4

Reactant 3

HCID 798IndoleHCID 2733210(2-Ethylphenyl)hydrazineHCID 147702072-Oxobicyclo[4.1.0]heptane-1-acetic Acid Ethyl Ester

Product 1

HCID 143022447-Ethyl-1,1a,2,3,8,8b-hexahydrocyclopropa[a]-carbazole-8b-acetic Acid

Procedure

The title compound was prepared from 2-oxobicyclo[4.1.0]heptane-1-acetic acid ethyl ester by a Fisher indole reaction with 2-ethylphenylhydrazine followed by ester hydrolysis as described in Example 1, Step 6, m.p. 154°-156° C. (foams).

Sources & evidence

ORD record
ord-416e5723af744c25bdb47d8ce776bcc9
Source dataset
uspto-grants-1989_10
Patent number
US04873257

Reaction notes

Loading…