Water → HCID 13662974, compound

HRID 1583367Notes

Reaction equation

HRID 1583367 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([CH3:16])[CH:10]=2)=[O:6].[C:17](Cl)(=[O:19])[CH3:18].O>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[N:8]([C:17](=[O:19])[CH3:18])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([CH3:16])[CH:10]=2)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 4715128methyl 6-methyl-1H-indole-2-carboxylate

Product 1

HCID 13662974HCID 13662974, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (4.70 g. of 50% dispersion in mineral oil) was added portionwise with stirring to a stirred solution of 6-methylindole-2-carboxylic acid methyl ester (18.0 g.) in dry N,N-dimethylformamide (100 ml.) and the mixture was stirred at room temperature for 1.5 hours. Acetyl chloride (8.0 g.) was then added dropwise with stirring and cooling and the resulting mixture was stirred at room temperature for 5 hours and then poured into water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with chloroform first gave mineral oil followed by pure product. Evaporation of the product-containing fractions gave a solid which are crystallized from methanol to give 1-acetyl-6-methylindole-2-carboxylic acid methyl ester (14.4 g.), m.p. 51°-53° C.

Workup

  1. stirringwith stirring
  2. temperaturecooling
  3. stirringthe resulting mixture was stirred at room temperature for 5 hours
  4. extractionThe mixture was extracted several times with ethyl acetate
  5. washthe combined extracts were washed with water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave an oil which
  9. customwas chromatographed on silica gel
  10. washElution with chloroform first gave mineral oil
  11. customEvaporation of the product-containing fractions
  12. customgave a solid which
  13. customare crystallized from methanol

Sources & evidence

ORD record
ord-beee842830c4416596f923deb8579f25
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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