Реакция #654812

Уравнение реакции

hydroxy-indole

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

p-carboxymethylphenylhydrazine hydrochloride

1,1-bis(hydroxymethyl)propanone

→

(3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   Температураat reflux for 1

Методика

The hydroxy-indole compound is readily prepared by literature method (P. L. Southwick, J. G. Cairns, L. A. Ernst, and A. S. Waggoner, 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 1 gives (3,3-dihydroxymethyl2-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.

Источник