Acetic Acid → 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

HRID 522224Notes

Reaction equation

HRID 522224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.C1N2CN3CN(C2)CN1C3.[C:21](O)(=[O:23])C>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[C:10]([CH:21]=[O:23])[C:3]=12

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 247295674-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (15 g, 98 mmol) and hexamethylenetetramine (25.00 g, 178 mmol) in aqueous acetic acid (33%, 15 mL) was heated at 100° C. overnight. After cooling, the mixture was poured into ice-water and stirred for several minutes. The solid material was collected by filtration, washed with water, and dried in vacuo to provide the title compound. MS (ESI+) m/z 181 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationThe solid material was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-68f1cb39036e44d1916b420b51ce5047
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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