Acetic Acid → 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

HRID 872041Notes

Reaction equation

C1N2CN3CN(C2)CN1C3.[C:11]([OH:14])(=O)[CH3:12].[NH:15]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2C=[CH:16]1>O>[NH:15]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[C:12]([CH:11]=[O:14])=[CH:16]1

Participants

Conditions

Temperature: 120 °C

Procedure

Hexamethylenetetramine (9.63 g) and acetic acid (20 ml) were added to a suspension of 1H-pyrrolo[2,3-b]pyridine (5.91 g) in water (40 ml) and it was stirred at 120° C. for 3 hours. The reaction mixture was cooled to room temperature, water (120 ml) was added and the mixture was stirred at room temperature for an hour. The precipitated crystalline was collected to give 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde (4.85 g) as a colorless powder.

Workup

temperatureThe reaction mixture was cooled to room temperature
stirringthe mixture was stirred at room temperature for an hour
customThe precipitated crystalline was collected

Sources & evidence

ORD record: ord-94dfa34d854e49659d01e6167705283e
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975252B2

Reaction notes

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