Diphenyl Ether → ETHYL 4-OXO-1,4-DIHYDROPYRROLO[1,2-B]PYRIDAZINE-3-CARBOXYLATE

HRID 347471Notes

Reaction equation

HRID 347471 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.[N:14]1([NH:19][CH:20]=[C:21]([C:27]([O:29]CC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15]1>>[O:29]=[C:27]1[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][NH:19][N:14]2[CH:15]=[CH:16][CH:17]=[C:18]12

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 10015075HCID 10015075, compound

Product 1

HCID 10104421ETHYL 4-OXO-1,4-DIHYDROPYRROLO[1,2-B]PYRIDAZINE-3-CARBOXYLATEYield 71%

Conditions

Temperature
220 °C

Procedure

A mixture of N-aminopyrrole (575 mg, 7.0 mmol, commercially available) and diethyl ethoxymethylenemalonate (1.82 g, 8.4 mmol) was heated at 125° C. for 2 hours to give crude diethyl 2-((1H-pyrrol-1-ylamino)methylene)malonate. To this intermediate was added diphenyl ether (2 mL). The reaction was put under nitrogen and heated at 220° C. for 2 hours, while allowing the ethanol formed in the reaction to be distilled off. The reaction was cooled to room temperature and purified by silica gel flash chromatography (eluted with 100% CH2Cl2) to give the title compound (1.03 g, 71%) as a yellow solid.

Workup

  1. customformed in the reaction
  2. distillationto be distilled off
  3. temperatureThe reaction was cooled to room temperature
  4. custompurified by silica gel flash chromatography (eluted with 100% CH2Cl2)

Sources & evidence

ORD record
ord-99fa87e0afcc4304a34620f75f7eb290
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

Loading…