Ammonium Hydroxide → 1H-Pyrrolo[2,3-b]pyridine-3-carboxamide

HRID 2108764Notes

Reaction equation

HRID 2108764 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:2].[NH4+].[OH-:13]>S(=O)(=O)(O)O>[NH:5]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:11]2[C:3]([C:1]([NH2:2])=[O:13])=[CH:4]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 103131951H-PYRROLO[2,3-B]PYRIDINE-3-CARBONITRILE

Product 1

HCID 126460351H-Pyrrolo[2,3-b]pyridine-3-carboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3-cyano-7-azaindole (3 g, 20.98 mmol) in concentrated sulfuric acid (50 mL) was stirred at room temperature for 1 h. The solution was slowly poured into ice and basified with concentrated NH4OH. The solution was concentrated under reduced pressure to produce brown residue which was extracted with acetone (4×100 mL). The organic extracts were dried and concentrated under reduced pressure to give title compound as a brown solid (3 g, 91%); Mass Spec.; MS 162 (M+1); 1H NMR (DMSO-d6; 500 MHz) 8.44(dd,1H),8.25(dd,1H), 8.14(s,1H), 7.45(brs,1H), 7.15(dd, 1H), 6.89(brs,1H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customto produce brown residue which
  3. extractionwas extracted with acetone (4×100 mL)
  4. customThe organic extracts were dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc3cbca9a6b0478891dfbc6e586c03f7
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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