Water → Pyrrolo[1,2-b]pyridazin-4(1H)-one

HRID 347472Notes

Reaction equation

HRID 347472 reaction equation
[O:1]=[C:2]1[C:7](C(OCC)=O)=[CH:6][NH:5][N:4]2[CH:13]=[CH:14][CH:15]=[C:3]12.[Na+].[Cl-].O>CS(C)=O>[NH:5]1[CH:6]=[CH:7][C:2](=[O:1])[C:3]2=[CH:15][CH:14]=[CH:13][N:4]12

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 10104421ETHYL 4-OXO-1,4-DIHYDROPYRROLO[1,2-B]PYRIDAZINE-3-CARBOXYLATE

Product 1

HCID 57415871Pyrrolo[1,2-b]pyridazin-4(1H)-oneYield 67.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 4-oxo-1,4-dihydropyrrolo[1,2-b]pyridazine-3-carboxylate (206 mg, 1.0 mmol), NaCl (64 mg, 1.1 mmol), water (0.054 mL, 3.0 mmol) and DMSO (2 mL) was heated at 150° C. for 3 hours. At the end of the reaction DMSO was distilled off and the residue was purified by silica gel flash chromatography (eluted with 1–10% EtOAc/CH2Cl2) to give the title compound (90 mg, 67%) as a light yellow solid.

Workup

  1. distillationwas distilled off
  2. customthe residue was purified by silica gel flash chromatography (eluted with 1–10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-b3551cdbfd064d4ba62240ba41e1392c
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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