2-Pyridone → HCID 13537712, compound

HRID 1583962Notes

Reaction equation

HRID 1583962 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].[K+].[Br-].[NH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=[O:21].[N-:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>CN(C=O)C>[N:22]1([C:16]([C:17]2[CH:18]=[C:19]([C:20]#[N:15])[C:1](=[O:2])[NH:8][C:12]=2[CH3:11])=[O:21])[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

6

Reactant 4

HCID 88712-PyridoneHCID 682631,1'-CarbonyldiimidazoleHCID 253877Potassium BromideHCID 3386966Imidazolate

Product 1

HCID 13537712HCID 13537712, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 0.20 g (1.1 mmol) of 11 in 10 ml DMF was added carbonyldiimidazole (0.223 g, 1.4 mmol). The solution was stirred for 24 hours at room temperature. Dimethylformamide was stripped off under reduced pressure giving an oil which crystallized upon further drying. The solid was washed with water and dried in the vacuum dessicator. Yellow solids were obtained: 0.11 g, 40% yield; mp=237°-238° C. with decomposition; NMR (DMSO-d6) δ 2.5 (s, 3H), 7.2 (d, 1H), 7.8 (d, 1H), 8.4 (2s, 2H); IR (KBr) 1670 cm-1 (C=O of pyridone), 1710 cm-1 (C=O of imidazolide).

Workup

  1. customgiving an oil which
  2. customcrystallized upon further drying
  3. washThe solid was washed with water
  4. customdried in the vacuum dessicator
  5. customYellow solids were obtained

Sources & evidence

ORD record
ord-88cbb06b78c746f9afd129425f3622f0
Source dataset
uspto-grants-1985_11
Patent number
US04555517

Reaction notes

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