Hydrochloric Acid → 1-Methyl-4,6-dichloroisatin

HRID 1369122

Reaction equation

HRID 1369122 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]2[C:5]=1[C:6](=[O:15])[C:7](=[O:14])[NH:8]2.I[CH3:17].Cl>C1COCC1>[CH3:17][N:8]1[C:9]2[C:5](=[C:4]([Cl:3])[CH:12]=[C:11]([Cl:13])[CH:10]=2)[C:6](=[O:15])[C:7]1=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2519084,6-Dichloroisatin

Product 1

HCID 185185371-Methyl-4,6-dichloroisatinYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 60% NaH (20.5 mg), 4,6-dichloroisatin (947 mg), and iodomethane (0.328 mL) in THF (20 mL) were stirred overnight at room temperature, poured into 1 N hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with sat. aqueous NaCl, dried over MgSO4, and concentrated. The residue was washed with hexane to give the title compound (849 mg, 84%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with sat. aqueous NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-ead5a8352e254e4fac6704b9d6f66aa2
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Linked notes

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