HCID 10735743, compound → 5-Hydroxy-1-methyl-3-(1-methylethoxy)-1H-indole-2-carboxamide

HRID 21588Notes

Reaction equation

HRID 21588 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11]CC3C=CC=CC=3)=[CH:8][CH:9]=2)[C:4]([O:19][CH:20]([CH3:22])[CH3:21])=[C:3]1[C:23]([NH2:25])=[O:24]>CO.[Pd]>[OH:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[C:3]([C:23]([NH2:25])=[O:24])=[C:4]2[O:19][CH:20]([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 10735743HCID 10735743, compound

Product 1

HCID 108481465-Hydroxy-1-methyl-3-(1-methylethoxy)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-methyl-(1-methylethoxy)-5-(phenylmethoxy)-1H-indole-2-carboxamide (2.1 g, 6.2 mmol) in 100 mL of methanol is hydrogenated using 0.5 g of 20% palladium on carbon catalyst. The catalyst is filtered and the filtrate evaporated. Recrystallization of the residue from aqueous acetonitrile gives. 0.87 g (58%) of product; mp 234°-237° C.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe filtrate evaporated
  3. customRecrystallization of the residue from aqueous acetonitrile
  4. customgives

Sources & evidence

ORD record
ord-743aa8cda3cf415686ad3230c8055753
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Reaction notes

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