Dimethyl Sulfate → HCID 18986254, compound

HRID 2396823Notes

Reaction equation

HRID 2396823 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([Cl:14])[C:9]([F:13])=[CH:10][CH:11]=2)[C:6](=[O:15])[CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+].S(OC)(O[CH3:22])(=O)=O>C(=O)(O)[O-].[Na+]>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([Cl:14])[C:9]([F:13])=[CH:10][CH:11]=2)[C:6]([O:15][CH3:22])=[CH:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 18986321HCID 18986321, compound

Product 1

HCID 18986254HCID 18986254, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2 g of 1-acetyl-4-chloro-5-fluoroindolin-3-one, 2 g of powdered sodium hydroxide and 30 ml of dimethyl sulfate was stirred at room temperature for 5 hours. After the addition of 250 ml of saturated sodium bicarbonate solution the mixture was stirred overnight and subsequently filtered. The residue was filtered in 150 ml of ether and 100 ml of ethyl acetate. The solution was dried over sodium sulfate, filtered and evaporated. There were obtained 2 g (95%) of 1-acetyl-4-chloro-5-fluoro-3-methoxyindole as greenish crystals with m.p. 114°-115°.

Workup

  1. stirringwas stirred overnight
  2. filtrationsubsequently filtered
  3. filtrationThe residue was filtered in 150 ml of ether
  4. dry with materialThe solution was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d41d7e4219e2476f87ff7963fbdf384b
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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