HCID 70382086, compound → HCID 70382030, compound

HRID 1762931Notes

Reaction equation

HRID 1762931 reaction equation
[ClH:1].[CH3:2][O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([C:15](=[O:19])[CH2:16][NH:17][CH3:18])[CH:11]=[CH:10][C:9]=2[OH:20])=[O:5]>CO.[Pd]>[ClH:1].[CH3:2][O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH:15]([OH:19])[CH2:16][NH:17][CH3:18])[CH:11]=[CH:10][C:9]=2[OH:20])=[O:5]

Participants

4

Reactant 1

HCID 70382086HCID 70382086, compound

Product 1

HCID 70382030HCID 70382030, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 896 mg of 4-methylaminoacetyl-7-hydroxyindole-2-carboxylic acid methyl ester hydrochloride in 30 ml of methanol is combined with 150 mg of 10% palladium-animal charcoal catalyst and hydrogenated under shaking at normal pressure. The reaction mixture is then filtered and the filtrate evaporated to dryness under vacuum. The residue is extracted by boiling with 20 ml of acetonitrile and the insoluble proportion is vacuum-filtered and recrystallized from ethanol, thus producing 232 mg of 4-(1-hydroxy-2-methylaminoethyl)- 7-hydroxyindole-2-carboxylic acid methyl ester hydrochloride, decomposition point 177°-180° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customthe filtrate evaporated to dryness under vacuum
  3. extractionThe residue is extracted
  4. filtrationthe insoluble proportion is vacuum-filtered
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d35897497cd6431494d109499645be32
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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