Reaction #2195471

Reaction equation

p-carboxymethylphenylhydrazine hydrochloride

1,1-bis(hydroxymethyl)propanone

hydroxy-indole

(2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid

→

(3,3-dihydroxymethyl-2-methyl-3-H-indol-5-yl)-acetic acid

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperatureat reflux for one minute

Procedure

The hydroxy-indole compound is readily prepared by a known method (P. L. Southwick, et al., One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmole, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for one minute gives (3,3-dihydroxymethyl-2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. The reaction of 3-bromopropyl-N,N-bis(carboxymethyl)amine, which was prepared as described in Example 5, with the intermediate indole and subsequent reaction of the indole intermediate with glutaconaldehyde dianil monohydrochloride (see Example 1) gives the desired product.

Source