Methanol → HCID 59335089, compound

HRID 1517963Notes

Reaction equation

HRID 1517963 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:14]([OH:16])=[O:15])=[CH:9][N:10]2[CH3:13])=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+].CO>O.[Ni]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:14]([OH:16])=[O:15])=[CH:9][N:10]2[CH3:13])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59334938HCID 59334938, compound

Product 1

HCID 59335089HCID 59335089, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

12 g 6-nitro-1-methyl-1H-indole-3-carboxylic acid are dissolved in 500 ml of water, 60 ml 1 N sodium hydroxide solution and 30 ml of methanol. 1.2 g Raney nickel are added and the mixture is hydrogenated for 26 hours at 1.5 bar. Then the catalyst is filtered off and the solvent is eliminated in vacuo. The residue is suspended in 100 ml of pyridine. 16.3 g 3,5-dichlorophenylsulphonyl chloride are added and the mixture is stirred overnight at ambient temperature. The pyridine is eliminated in vacuo. The residue is divided between water and ethyl acetate and the pH is adjusted to 5 by the addition of citric acid. The aqueous phase is extracted 3 times with ethyl acetate and the combined organic phases are dried on magnesium sulphate. After elimination of the solvents the residue is chromatographed on silica gel (dichloromethane/methanol/acetic acid 95:5:1 to 89:10:1)

Workup

  1. filtrationThen the catalyst is filtered off
  2. addition16.3 g 3,5-dichlorophenylsulphonyl chloride are added
  3. additionthe pH is adjusted to 5 by the addition of citric acid
  4. extractionThe aqueous phase is extracted 3 times with ethyl acetate
  5. customthe combined organic phases are dried on magnesium sulphate
  6. customAfter elimination of the solvents the residue is chromatographed on silica gel (dichloromethane/methanol/acetic acid 95:5:1 to 89:10:1)

Sources & evidence

ORD record
ord-43b5e5da32ad401291441138e7239e06
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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