1H-Indol-2-ol → (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid

HRID 498905Notes

Reaction equation

HRID 498905 reaction equation
OC1NC2C(C=1)=CC=CC=2.CC1C(C)(C)C2C(=CC=C(CC(O)=O)C=2)N=1.Cl.[C:28]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38]N)=[CH:34][CH:33]=1)([OH:30])=[O:29].[OH:40][CH2:41][CH:42]([CH2:46][OH:47])[C:43](=O)[CH3:44]>C(O)(=O)C>[OH:40][CH2:41][C:42]1([CH2:46][OH:47])[C:36]2[C:35](=[CH:34][CH:33]=[C:32]([CH2:31][C:28]([OH:30])=[O:29])[CH:37]=2)[N:38]=[C:43]1[CH3:44]

Participants

6

Reactant 4

HCID 655311H-Indol-2-olHCID 138998154-Hydroxy-3-hydroxymethyl-2-butanoneHCID 141176372,3,3-trimethyl-3H-indol-5-yl-acetic acidHCID 15618594(4-Hydrazinophenyl)acetic acid hydrochloride

Product 1

HCID 21337716(3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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.

Workup

  1. temperatureat reflux for one minute

Sources & evidence

ORD record
ord-6a2c87bfc5b345d5815644f5ee4b926d
Source dataset
uspto-grants-2010_08
Patent number
US07767194B2

Reaction notes

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