Sodium Hydroxide → 3-(2carboxyprop-1-enyl)-N-(3-pyridyl)indole

HRID 485348Notes

Reaction equation

HRID 485348 reaction equation
C([O:3][C:4]([C:6]([CH3:23])=[CH: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:5])C.[OH-].[Na+]>CO.O>[C:4]([C:6]([CH3:23])=[CH: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:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 539181563-[2-(ethoxycarbonyl)prop-1-enyl]-N-(3-pyridyl)indole

Product 1

HCID 545426033-(2carboxyprop-1-enyl)-N-(3-pyridyl)indole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.1 g of 3-[2-(ethoxycarbonyl)-prop-1-enyl)-N-(3-pyridyl)indole, and 0.288 g of sodium hydroxide in 10 ml of methanol and 10 ml of water is heated under reflux for 2 hours, cooled and evaporated. The resulting oil is redissolved in 10 ml of ice water and is neutralized with 0.59 ml of concentrated hydrochloric acid. The resulting solid is filtered and dried to yield 3-(2carboxyprop-1-enyl)-N-(3-pyridyl)indole, m.p. 213°-215°.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturecooled
  3. customevaporated
  4. dissolutionThe resulting oil is redissolved in 10 ml of ice water
  5. filtrationThe resulting solid is filtered
  6. customdried

Sources & evidence

ORD record
ord-7fda04becbe44a579bd74c36533edeea
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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