Dimethyl Sulfate → HCID 117622785, compound

HRID 56610Notes

Reaction equation

HRID 56610 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8](=[O:13])[NH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(OC)(O[CH3:18])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.ClCCl>[CH3:18][N:9]1[C:8](=[O:13])[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[NH:10]1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 32644791,2-Dihydro-6-nitro-3H-indazol-3-one

Product 1

HCID 117622785HCID 117622785, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

1.66 g (9.27 mmol) of 6-nitro-1,2-dihydro-3H-indazol-3-one were initially charged in 20 ml of DMF, and 1.75 ml (18.5 mmol, 2.0 eq.) of dimethyl sulphate were added. The reaction mixture was heated at 60° C. for 8 h and then diluted with dichloromethane and shaken with saturated aqueous sodium carbonate solution. The aqueous phase was washed three times each with dichloromethane and with ethyl acetate and the organic fractions were discarded. Using 4N aqueous hydrochloric acid, the aqueous phase was then carefully adjusted to pH 4.5 and extracted three times with ethyl acetate. These combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel 50, mobile phase: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate/methanol 15:1), giving the title compound. Yield: 770 mg (43% of theory)

Workup

  1. washThe aqueous phase was washed three times each with dichloromethane
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThese combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography (silica gel 50, mobile phase: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate/methanol 15:1)

Sources & evidence

ORD record
ord-93ab0baae5db43f58a7f35b11b7f61fa
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

Loading…