Sulfuric Acid → 6-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877665Notes

Reaction equation

HRID 877665 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([Cl:10])=[C:8]([C:11]#[N:12])[CH:7]=[N:6][N:5]2[CH:13]=1.[OH:14]S(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([Cl:10])=[C:8]([C:11]([NH2:12])=[O:14])[CH:7]=[N:6][N:5]2[CH:13]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 682911366-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carbonitrile

Product 1

HCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamideYield 89%

Conditions

Temperature
55 °C

Procedure

To a 50 mL round bottom flask was added 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carbonitrile (12 g, 0.046 mol) and concentrated H2SO4 (60 mL). The reaction mixture was heated at 55° C. for 2 hours then cooled to room temperature and slowly diluted with ice water to precipitate the product which was collected by vacuum filtration, rinsed with water and dried to yield 11.2 g (89%) of the title compound as a yellow solid. HPLC (condition P): retention time=7.780 min. LCMS (condition C): m/z 274.0, 276.0 −ve. H1 NMR (400 MHz, DMSO-d6) δ ppm: 8.32 (2H, s), 8.05 (1H, s), 7.90 (1H, s), 7.01 (1H, s).

Workup

  1. temperaturethen cooled to room temperature
  2. customto precipitate the product which
  3. filtrationwas collected by vacuum filtration
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-a7fe1a9fa43145b9a40e20bd6e52f338
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

Loading…