Indole → 1H-Indole-3-propanoic acid

HRID 1904168Notes

Reaction equation

HRID 1904168 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12]>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:12][CH2:11][C:10]([OH:14])=[O:13])=[CH:2]1

Participants

4

Reactant 2

HCID 798IndoleHCID 6581Acrylic Acid

Product 1

HCID 37441H-Indole-3-propanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Reaction of indole XXI with acrylic acid in the presence of acetic acid affords the indole-3-propionic acid. Esterification, alkylation of the indole nitrogen, if desired, and trifluoroacetic acid hydrolysis gives rise to indoles of Formula VII in which R is (CH2)mCO2R9, m is 2 and R2 is H or C1 -C3 alkyl. ##STR29##

Sources & evidence

ORD record
ord-07516815785844fb8489aadc31c37404
Source dataset
uspto-grants-1989_06
Patent number
US04836846

Reaction notes

Loading…