2-(1-methyl-1H-indol-3-yl)acetic acid → Indole

HRID 1418630Notes

Reaction equation

HRID 1418630 reaction equation
[C:1]([CH2:3][CH:4]([N:6]1[C:18]2C3N(C)C4C=CC=CC=4C=3C3C(=O)NC(=O)C=3[C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:5])#[N:2].[C:32]([CH2:34][CH:35]([N:37]1C2[C:40](=[CH:41][CH:42]=[CH:43]C=2)[CH:39]=[CH:38]1)C)#[N:33].C[N:47]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:49](CC(O)=O)=[CH:48]1>C(#N)C>[C:1]([CH2:3][CH:4]([N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:18]1)[CH3:5])#[N:2].[CH2:41]1[CH2:42][CH2:43][N:33]2[C:38](=[N:37][CH2:35][CH2:34][CH2:32]2)[CH2:39][CH2:40]1.[CH3:51]/[CH:50]=[CH:49]/[C:48]#[N:47].[NH:47]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48]1

Participants

8

Reactant 3

HCID 2541662-(1-methyl-1H-indol-3-yl)acetic acidHCID 21216820HCID 21216820, compoundHCID 23221070HCID 23221070, compound

Product 4

HCID 798IndoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 637921CrotononitrileHCID 23221070HCID 23221070, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

12-(3-cyano-2-propyl)-6,7,12,13-tetrahydro-13-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole; yellow crystals which decompose from about 270° C. The 3-[1-(3-cyano-2-propyl)-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrol-3,5-dione used as starting material (red amorphous powder; decomp. point about 218°-226° C.) is prepared analogously to EP 0 328 026 from 1-(3-cyano-2-propyl)-indole and 1-methyl-3-indolylacetic acid. 1-(3-Cyano-2-propyl)-indole is prepared in low yield by the base-catalysed (DBU) addition of crotonitrile to indole in acetonitrile.

Workup

  1. customdecompose from about 270° C

Sources & evidence

ORD record
ord-0d759dd6ecd64917b3a950a4639d3a2e
Source dataset
uspto-grants-1999_03
Patent number
US05883114

Reaction notes

Loading…