Methanol → HCID 20270179, compound

HRID 485358Notes

Reaction equation

HRID 485358 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH3:28]O>>[CH3:28][O:2][C:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 134903525-[1-(Pyridin-3-yl)-1H-indol-3-yl]pentanoic acid

Product 1

HCID 20270179HCID 20270179, compound

Procedure

A solution of 5.0 g of 3-(4-carboxybutyl)-N-(3-pyridyl)indole in 50 ml of methanol is refluxed under nitrogen with 0.25 g of concentrated sulfuric acid for 2 hours. The reaction mixture is cooled and evaporated and partitioned between 50 ml of ether and 50 ml of ice-cold, saturated sodium bicarbonate solution. The organic phase is separated, dried over potassium carbonate and evaporated to yield 3-(4-methoxycarbonylbutyl)-N-(3-pyridyl)indole.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customevaporated
  3. custompartitioned between 50 ml of ether and 50 ml of ice-cold, saturated sodium bicarbonate solution
  4. customThe organic phase is separated
  5. dry with materialdried over potassium carbonate
  6. customevaporated

Sources & evidence

ORD record
ord-a7fdbf91256c4f89b073ae42076ba114
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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