HCID 70381469, compound → HCID 13105642, compound

HRID 1762932Notes

Reaction equation

HRID 1762932 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([C:15](=[O:21])[CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])[CH:11]=[CH:10][C:9]=2[OH:22])=[O:5].[H][H]>CO.[Pd]>[CH3:2][O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH:15]([OH:21])[CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])[CH:11]=[CH:10][C:9]=2[OH:22])=[O:5]

Participants

5

Reactant 2

HCID 70381469HCID 70381469, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13105642HCID 13105642, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.6 g of 7-hydroxy-4-isopropylaminoacetylindole-2-carboxylic acid methyl ester hydrochloride in 80 ml of methanol is combined with 300 mg of 10% palladium-animal charcoal and shaken for 21/4 hours under normal pressure with hydrogen. The reaction mixture is then filtered and the filtrate evaporated to dryness under vacuum. The residue is triturated with acetonitrile, cooled to 0° C., and filtered, thus obtaining 1.41 g of 4-(1-hydroxy-2-isopropylaminoethyl)-7-hydroxyindole-2-carboxylic acid methyl ester, decomposition point 137°-139° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customthe filtrate evaporated to dryness under vacuum
  3. customThe residue is triturated with acetonitrile
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a35f7457a6ae4802bb5f1fc25a072b49
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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