Реакция #722954

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.

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