Ammonium Hydroxide → 3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole

HRID 64678Notes

Reaction equation

HRID 64678 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH:2]=1.[Cl-].[CH2:17]([O:19][C:20](=[O:27])[CH2:21][CH2:22][CH2:23][C:24](O)=[O:25])[CH3:18].[OH-].[NH4+]>C(Cl)Cl>[O:25]=[C:24]([C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:8]=1)[CH2:23][CH2:22][CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:27]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 134903481-(pyridin-3-yl)-1H-indoleHCID 53445130HCID 53445130, compound

Product 1

HCID 136726963-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 10.0 g of N-(3-pyridyl)-indole (J. Chem. Soc. (C), 85, 1970) and 13.8 g of glutaric acid monoethyl ester chloride in 90 ml of methylene chloride is added dropwise over a period of 3 hours a solution of 20.1 g of stannic chloride in 60 ml of methylene chloride. The reaction mixture is stirred at room temperative overnight. The reaction mixture is cooled to 10°-15° and 150 ml of 14% aqueous ammonium hydroxide is added. The organic layer is separated, washed with water and dried over sodium sulfate to yield 3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole, melting at 95°-97°.

Workup

  1. temperatureThe reaction mixture is cooled to 10°-15°
  2. customThe organic layer is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-9855b684a0c147dfa19c713f124aabf7
Source dataset
uspto-grants-1986_09
Patent number
US04609733

Reaction notes

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