Water → 3-(4-ethoxycarbonylbutyl)N-(3-pyridyl)-indole

HRID 64684Notes

Reaction equation

HRID 64684 reaction equation
O=[C:2]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl-].[Al+3].[Cl-].[Cl-].O.[OH-].[Na+]>C(Cl)Cl>[CH2:9]([O:8][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 136726963-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole

Product 1

HCID 134903513-(4-ethoxycarbonylbutyl)N-(3-pyridyl)-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.5 g of 3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)-indole in 15 ml of methylene chloride are added first 0.40 g of aluminum chloride and subsequently 0.175 g of dimethylamine borane complex. The reaction mixture is stirred at room temperature for 24 hours. The mixture is cooled to 0° and 10 ml of water are added dropwise. After ten minutes, 35 ml of 1N aqueous sodium hydroxide are added to adjust pH to 8. The methylene chloride layer is separated, the aqueous layer is further extracted with methylene chloride; the methylene chloride extracts are combined, washed with water, dried and evaporated to dryness to yield 3-(4-ethoxycarbonylbutyl)N-(3-pyridyl)-indole. Hydrolysis with dilute sodium hydroxide yields 3-(4-carboxybutyl)-N-(3-pyridyl)-indole.

Workup

  1. temperatureThe mixture is cooled to 0°
  2. waitAfter ten minutes
  3. customThe methylene chloride layer is separated
  4. extractionthe aqueous layer is further extracted with methylene chloride
  5. washwashed with water
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-da5b54f0883f484ea4c3058bd9e91bfd
Source dataset
uspto-grants-1986_09
Patent number
US04609733

Reaction notes

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