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

HRID 2261563Notes

Reaction equation

HRID 2261563 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C1N2CN3CN(C2)CN1C3.[C:20](O)(=[O:22])C>O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:20]=[O:22])=[CH:2]1

Participants

5

Reactant 3

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

Product 1

HCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 1H-Pyrrolo[2,3-b]pyridine (1, 16.0 g, 135 mmol) in water (110 mL), were added hexamethylenetetramine (26.0 g, 185 mmol), and acetic acid (55.0 mL, 967 mmol). The reaction was refluxed for 12 hours. Water (329 mL) was added and the reaction was cooled to room temperature. The reaction was filtrated and washed with water to give compound (46, 15.0 g, 76%). MS (ESI)[M+H+]+=147.

Workup

  1. temperatureThe reaction was refluxed for 12 hours
  2. filtrationThe reaction was filtrated
  3. washwashed with water
  4. customto give compound (46, 15.0 g, 76%)

Sources & evidence

ORD record
ord-1de8a1defc6a449cb433c7d2a454a9bb
Source dataset
uspto-grants-2010_12
Patent number
US07846941B2

Reaction notes

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