Aluminium lithium hydride → 2-(1H-Pyrrolo[2,3-c]pyridin-3-yl)ethan-1-amine

HRID 731602Notes

Reaction equation

HRID 731602 reaction equation
O=[C:2]([C:6]1[C:14]2[C:9](=[CH:10][N:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[C:3]([NH2:5])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[NH2:5][CH2:3][CH2:2][C:6]1[C:14]2[C:9](=[CH:10][N:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22663070HCID 22663070, compound

Product 1

HCID 226629962-(1H-Pyrrolo[2,3-c]pyridin-3-yl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-oxo-2-(1H-pyrrolo[2,3-c]pyridin-3-yl)acetamide (1 eq.) in ether is treated with lithium aluminum hydride (4 eq.), heated at reflux temperature for 8 h, cooled to 0° C. and quenched by addition of Rochelle's salt solution. The reaction mixture is extracted with CH2Cl2; the combined extracts are dried over MgSO4 and concentrated in vacuo to afford the title 6-azatryptamine product, which is used directly in step 4, below.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 8 h
  3. customquenched by addition of Rochelle's salt solution
  4. extractionThe reaction mixture is extracted with CH2Cl2
  5. dry with materialthe combined extracts are dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6b8d35b26824a86a8cd8298a86aa4d1
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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