Acetic Acid → 1H-Pyrrolo(2,3-b)pyridine-2-carbaldehyde

HRID 489731Notes

Reaction equation

HRID 489731 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.C1N2CN3CN(C2)CN1C3.[C:20](O)(=[O:22])C>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[C:2]1[CH:20]=[O:22]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 92221H-Pyrrolo(2,3-b)pyridine

Product 1

HCID 218736801H-Pyrrolo(2,3-b)pyridine-2-carbaldehydeYield 58%

Procedure

To a solution of 7-Azaindole (Aldrich Chemical Co. Cat No. A9,550-2, 4.12 g, 34.9 mmol) in 33% acetic acid (43 ml) was added Hexamethylenetetramine (7.3 g, 5.2 mmol) and the reaction was heated at reflux for 6 hours. The reaction mixture was cooled to room temperature and diluted with ice water (100 ml). The mixture was then left at 0° C. for 18 h. to crystallize product. The beige powder was filtered and washed with water to provide 7-azaindole-2-carboxaldehyde (2.95 g, 58%). 1H NMR (DMSO-d6) δ:7.28 (1H, dd, J=4.8 Hz, 7.9 Hz), 8.37 (1H, dd, J=1.6 Hz, 4.8 Hz), 8.42 (1H, dd, J=1.6 Hz, 7.9 Hz), 8.47 (1H, s), 9.94 (s, 1H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 6 hours
  3. customto crystallize product
  4. filtrationThe beige powder was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-c2592e9705864d8eba7fe25c66918e78
Source dataset
uspto-grants-2005_12
Patent number
US06979696B2

Reaction notes

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