Indole → 1H-Indole-1-propionic acid

HRID 346800Notes

Reaction equation

HRID 346800 reaction equation
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.C[O:13][C:14](=[O:18])[CH2:15][CH2:16]Br.O>CS(C)=O>[N:3]1([CH2:16][CH2:15][C:14]([OH:18])=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 14797Potassium HydroxideHCID 76934Methyl 3-bromopropanoate

Product 1

HCID 811391H-Indole-1-propionic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

KOH (11.5 g, 0.2 mol.) was added to a solution of indole (5.0 g, 40.0 mmol.) and 3-bromopropionic acid methyl ester (4.37 ml, 40 mmol.) in DMSO (35 ml), and stirring was carried out for 24 h at RT. For working up, water (50 ml) was added to the mixture, washing was carried out with ether (5×20 ml), and the aqueous phase was adjusted to pH 4 with 1M HCl and extracted with ether (5×20 ml). The combined extracts were dried, filtered and concentrated. Chromatography with methanol yielded 3-indol-1-ylpropionic acid in a yield of 3.8 g (white solid, m.p. 54–56° C.).

Workup

  1. washwashing
  2. extractionextracted with ether (5×20 ml)
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-15e28290268049f2a8aff8d7b36d2088
Source dataset
uspto-grants-2007_02
Patent number
US07173045B2

Reaction notes

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