Water → HCID 20270209, compound

HRID 485351Notes

Reaction equation

HRID 485351 reaction equation
[C:1]([C:6]1[N:7]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)(OCC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[OH:2][CH2:1][C:6]1[N:7]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20270210HCID 20270210, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20270209HCID 20270209, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5.0 g of 2-carboethoxy-N-(3-pyridyl)indole in 75 ml of dry ether is cooled to 5° and 0.7 g of lithium aluminum hydride is added in portions. Cooling is suspended and the reaction mixture is stirred at room temperature under nitrogen for 18 hours and re-cooled to 5°. Sequential addition of 0.7 ml of water, 0.7 ml of 15% sodium hydroxide and 2.1 ml of water produces a fine precipitate which is removed by filtration through celite. The filtrate is dried over sodium sulfate and evaporated to yield crude 2-hydroxymethyl-N-(3-pyridyl)indole which is used without further purification; Rf (9:1 toluene:methanol, silica gel)=0.2.

Workup

  1. temperatureCooling
  2. temperaturere-cooled to 5°
  3. customproduces a fine precipitate which
  4. customis removed by filtration through celite
  5. dry with materialThe filtrate is dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d71976b25840429c82e60593621f22cf
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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