Methanol → methyl 6-methyl-1H-indole-2-carboxylate

HRID 1583366Notes

Reaction equation

HRID 1583366 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([OH:13])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[CH3:19]O>>[CH3:19][O:12][C:11]([C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([CH3:1])[CH:10]=2)=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 24813Phosphorus oxychlorideHCID 31633966-Methyl-1H-indole-2-carboxylic acid

Product 1

HCID 4715128methyl 6-methyl-1H-indole-2-carboxylate

Procedure

A solution of 6-methylindole-2-carboxylic acid (38.2 g.) in methanol (400 ml.) containing phosphorus oxychloride (5 ml.) was heated under reflux for 4 hours and then evaporated. The residue was dissolved in chloroform and the solution was washed successively with water and sodium bicarbonate solution and then dried (Na2SO4). Evaporation of the solvent gave a solid which was crystallized from methanol to give 6-methylindole-2-carboxylic acid methyl ester (28.1 g.), m.p. 128°-131° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customevaporated
  4. dissolutionThe residue was dissolved in chloroform
  5. washthe solution was washed successively with water and sodium bicarbonate solution
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave a solid which
  9. customwas crystallized from methanol

Sources & evidence

ORD record
ord-d885f50433e44c1e87296268805ce8f0
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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