Hydrochloric Acid → HCID 59276872, compound

HRID 1807434Notes

Reaction equation

HRID 1807434 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1.[C:18](=O)([O-])[O-].[K+].[K+].CI.Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:18][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59277341HCID 59277341, compound

Product 1

HCID 59276872HCID 59276872, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

230 mg 1-(1H-imidazol-2-yl)-5-nitro-2,3-dihydro-1H-indole are dissolved in 6 ml dimethylformamide, combined with 200 mg potassium carbonate and 75 μl methyl iodide and stirred overnight at ambient temperature. The mixture is divided between ethyl acetate and 2 N hydrochloric acid and the aqueous phase is washed twice with dichloromethane. Then the pH of the aqueous phase is adjusted to 12 by the addition of 40% sodium hydroxide solution and it is extracted with dichloromethane. The organic phase is washed with saturated sodium chloride solution and dried on magnesium sulphate. The solvents are eliminated in vacuo and the residue is chromatographed on silica gel (dichloromethane/methanol 99:1 to 90:10).

Workup

  1. washthe aqueous phase is washed twice with dichloromethane
  2. additionThen the pH of the aqueous phase is adjusted to 12 by the addition of 40% sodium hydroxide solution and it
  3. extractionis extracted with dichloromethane
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. customdried on magnesium sulphate
  6. customthe residue is chromatographed on silica gel (dichloromethane/methanol 99:1 to 90:10)

Sources & evidence

ORD record
ord-85c9f46dc74641c3aefc5d123db1e0e3
Source dataset
uspto-grants-2013_01
Patent number
US08357689B2

Reaction notes

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