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

HRID 2117074Notes

Reaction equation

HRID 2117074 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-c3d6a30045ac4d89b822000ee71d420c
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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