Aluminium lithium hydride → 2-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethanamine

HRID 731598Notes

Reaction equation

HRID 731598 reaction equation
O=[C:2]([C:6]1[C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:9]=2[NH:8][CH:7]=1)[C:3]([NH2:5])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[NH:8]1[C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:6]([CH2:2][CH2:3][NH2:5])=[CH:7]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 226630372-Oxo-2-(1H-pyrrolo[3,2-C]pyridin-3-YL)-acetamide

Product 1

HCID 226629862-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-oxo-2-(1H-pyrrolo[3,2-c]pyridin-3-yl)-acetamide (1 eq.) in ether is treated with lithium aluminum hydride (4 eq.), refluxed for 8 h, cooled to 0° C. and quenched by addition of Rochelle's salt solution. The reaction mixture is extracted with CH2Cl2. The extracts are combined dried over MgSO4 and concentrated in vacuo to give the title amine product, which is used as is in step 9, below.

Workup

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

Sources & evidence

ORD record
ord-33dd4a21c8004c9c8d51c6ced9956fde
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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