Hydrochloric Acid → HCID 22627192, compound

HRID 278124Notes

Reaction equation

HRID 278124 reaction equation
[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([NH2:17])=[O:16])=[CH:12][CH:13]=2)[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-])=O)[C:7]=1[CH2:28][CH2:29][CH3:30])(=[O:5])[CH:2]([CH3:4])[CH3:3].[ClH:31]>CO.[Pd].C(Cl)(Cl)Cl>[ClH:31].[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=2)[C:6]([C:1](=[O:5])[CH:2]([CH3:3])[CH3:4])=[C:7]1[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 22627344HCID 22627344, compound

Product 1

HCID 22627192HCID 22627192, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent3×HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 3-isobutyryl-1-(2-nitrobenzyl)-2-propylindole-6-carboxamide (316 mg) in methanol (10 ml) was hydrogenated over 10% palladium on carbon at 20° C. for 6 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of methanol and chloroform 1:30) to give an oil which was dissolved in a mixture of chloroform (10 ml) and methanol (20 ml). To this solution was added 10% hydrogen chloride in methanol (0.9 ml), and the mixture was stirred at 20° C. for 1 hour and evaporated in vacuo. The residue was recrystallized from a mixture of methanol and diisopropyl ether to give 1-(2-aminobenzyl)-3-isobutyryl-2-propylindole-6-carboxamide hydrochloride (415 mg) as colorless crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed on silica gel eluting with a mixture of methanol and chloroform 1:30)
  4. customto give an oil which
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-5d375438f6814f6590b8e4e644e29e38
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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