1H-Indole-2-carboxylic acid, 4-(2-aminoacetyl)-7-hydroxy-, methyl ester, hydrochloride (1:1) → HCID 70381806, compound

HRID 1762930Notes

Reaction equation

HRID 1762930 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:18])[CH2:16][NH2:17])[CH:11]=[CH:10][C:9]=2[OH:19])=[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:18])[CH2:16][NH2:17])[CH:11]=[CH:10][C:9]=2[OH:19])=[O:5]

Participants

4

Reactant 1

HCID 703827461H-Indole-2-carboxylic acid, 4-(2-aminoacetyl)-7-hydroxy-, methyl ester, hydrochloride (1:1)

Product 1

HCID 70381806HCID 70381806, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.14 g of 4-aminoacetyl-7-hydroxyindole-2-carboxylic acid methyl ester hydrochloride in 200 ml of methanol is combined with 110 mg of 10% palladium catalyst on active carbon and hydrogenated for 3 hours under shaking at normal pressure. The reaction mixture is then filtered and the filtrate evaporated to dryness. The residue is vigorously stirred with acetone/methanol 9/1; the resultant product is filtered off and dried under vacuum, thus obtaining 1.0 g of 4-(2-amino-1-hydroxyethyl)-7-hydroxyindole-2-carboxylic acid methyl ester hydrochloride, decomposition point 280° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customthe filtrate evaporated to dryness
  3. stirringThe residue is vigorously stirred with acetone/methanol 9/1
  4. filtrationthe resultant product is filtered off
  5. customdried under vacuum

Sources & evidence

ORD record
ord-58ee602054fc4a4681d8c14944923d3a
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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