Diazomethane diethylether → Methyl 4-chloro-3,7-dimethylindole-2-carboxylate

HRID 361612

Reaction equation

HRID 361612 reaction equation
[N+](=[CH2:3])=[N-].CCOCC.[Cl:9][C:10]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]2[C:11]=1[C:12]([CH3:23])=[C:13]([C:20]([OH:22])=[O:21])[NH:14]2>CCOCC>[Cl:9][C:10]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]2[C:11]=1[C:12]([CH3:23])=[C:13]([C:20]([O:22][CH3:3])=[O:21])[NH:14]2

Participants

4

Reactant 2

HCID 21186548Diazomethane diethyletherHCID 541380234-Chloro-3,7-dimethylindole-2-carboxylic acid

Product 1

HCID 54167277Methyl 4-chloro-3,7-dimethylindole-2-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An excess diazomethane ether solution was added to an ether solution of 0.50 g (2.24 mmol) of 4-chloro-3,7-dimethylindole-2-carboxylic acid under ice-cooling. The reaction mixture was allowed to stand for 30 minutes and then washed with 1N HCl aqueous solution and aqueous saturated sodium chloride solution. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide white crystals. The crude crystals were purified by silica gel column chromatography to provide 0.41 g of white crystals. Yield: 77%

Workup

  1. temperaturecooling
  2. washwashed with 1N HCl aqueous solution and aqueous saturated sodium chloride solution
  3. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto provide white crystals
  6. customThe crude crystals were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5c78a918d90a45fd82ec6dcd9951ca10
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Linked notes

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