4H-pyran-4-one → 8-(4-Oxo-1,4-dihydropyridin-1-yl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one

HRID 5803

Reaction equation

HRID 5803 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[CH:5][C:6]2[C:15]3[CH:10]([CH2:11][C:12](=[O:16])[NH:13][N:14]=3)[CH2:9][CH2:8][C:7]=2[CH:17]=1.O1[CH:23]=[CH:22][C:21](=[O:24])[CH:20]=[CH:19]1>O>[O:24]=[C:21]1[CH:22]=[CH:23][N:2]([C:3]2[CH:4]=[CH:5][C:6]3[C:15]4[CH:10]([CH2:11][C:12](=[O:16])[NH:13][N:14]=4)[CH2:9][CH2:8][C:7]=3[CH:17]=2)[CH:19]=[CH:20]1

Participants

4

Reactant 2

HCID 79684H-pyran-4-oneHCID 197942148-amino-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one hydrochloride

Product 1

HCID 197942298-(4-Oxo-1,4-dihydropyridin-1-yl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-oneYield 10.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 8-amino-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one hydrochloride (1.5 g) and 4H-pyran-4-one (0.84 g) in water (40 ml) was heated under reflux for 2 hours in a nitrogen atmosphere. The resultant solid was washed with dilute hydrochloric acid to give a crude product, 0.5 g. Purification by column chromatography (silica gel, 9:1 chloroform: methanol) gave the title compound 0.18 g, m.p. >300° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours in a nitrogen atmosphere
  3. washThe resultant solid was washed with dilute hydrochloric acid
  4. customto give a crude product, 0.5 g
  5. customPurification by column chromatography (silica gel, 9:1 chloroform: methanol)

Sources & evidence

ORD record
ord-59c565222c524969851c7e1b747f4739
Source dataset
uspto-grants-1993_09
Patent number
US05246928

Linked notes

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