Dimethyl Sulfate → HCID 18986212, compound

HRID 2396825Notes

Reaction equation

HRID 2396825 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[C:6](=[O:14])[CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+].S(OC)(O[CH3:21])(=O)=O>C(=O)(O)[O-].[Na+]>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[C:6]([O:14][CH3:21])=[CH:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 189863261-Acetyl-5-fluoro-1,2-dihydro-3H-indol-3-one

Product 1

HCID 18986212HCID 18986212, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1.6 g of 1-acetyl-5-fluoroindolin-3-one, 1.9 g of powdered sodium hydroxide and 28 ml of dimethyl sulfate was stirred at room temperature for two hours. After the addition of 240 ml of saturated sodium bicarbonate solution the mixture was stirred overnight and subsequently filtered. The residue was taken up in 100 ml of ether and 100 ml of ethyl acetate. The solution was dried over sodium sulfate, filtered and evaporated. There were obtained 1.47 g (86%) of 1-acetyl-5-fluoro-3-methoxyindole as greenish crystals with m.p. 124°-125°.

Workup

  1. stirringwas stirred overnight
  2. filtrationsubsequently filtered
  3. dry with materialThe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d458808d652b46499f344d6e802f1ed4
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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