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Ammonia → 7-(4-Oxo-1,4-dihydropyridin-1-yl)-[5H1indeno[1,2-c]-pyridazin-3(2H)-one

HRID 5802
Notes
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Reaction equation

HRID 5802 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:8]1=[N:9][NH:10][C:11](=[O:13])[CH:12]=[C:7]1[CH2:6]2.O1[CH:22]=[CH:21][C:20](=[O:23])[CH:19]=[CH:18]1.N>O>[O:23]=[C:20]1[CH:21]=[CH:22][N:2]([C:3]2[CH:4]=[C:5]3[C:14](=[CH:15][CH:16]=2)[C:8]2=[N:9][NH:10][C:11](=[O:13])[CH:12]=[C:7]2[CH2:6]3)[CH:18]=[CH:19]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 222AmmoniaHCID 79684H-pyran-4-oneHCID 197942087-amino-[5H]-indeno[1,2-c]pyridazin-3[2H]-one hydrochloride

Product 1

HCID 197942107-(4-Oxo-1,4-dihydropyridin-1-yl)-[5H1indeno[1,2-c]-pyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 7-amino-[5H]indeno[1,2-c]pyridazin-3(2H)-one hydrochloride (1.0 g) and 4H-pyran-4-one (0.48 g) in water (10 ml) was heated under reflux for 1 hour in a nitrogen atmosphere. The warm mixture was neutralised with aqueous ammonia to give a solid, 0.9 g, m.p. >300° C. This solid was triturated with warm dilute hydrochloric acid and washed with water to give the title compound, 0.42 g, m.p. >300° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour in a nitrogen atmosphere
  3. customto give a solid, 0.9 g, m.p. >300° C
  4. customThis solid was triturated
  5. temperaturewith warm dilute hydrochloric acid
  6. washwashed with water

Sources & evidence

ORD record
ord-f6081b4f6c874294b9305d5620438d99
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05246928

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes