Réaction #582504

Équation de réaction

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

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   Températureat reflux for one minute

Mode opératoire

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