Ethanol → HCID 19610849, compound

HRID 1602204Notes

Reaction equation

HRID 1602204 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:10]1[C:11](=[O:22])[C:12]2[C:17]([C:18](=O)[C:19]=1Cl)=[CH:16][CH:15]=[CH:14][CH:13]=2.C([OH:25])C>>[O:22]=[C:11]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[C:18]2[N:1]=[C:2]3[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]3[C:19]=2[C:10]1=[O:25]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8342DichloneHCID 153472-Amino-3-methylpyridine

Product 1

HCID 19610849HCID 19610849, compoundYield 52%

Procedure

4.76 g (44 mmol) of 2-amino-3-methylpyridine in solution in 50 mL of ethanol are added to a suspension of 10 g (44 mmol) of 2,3-dichloro-1,4-dihydro-1,4-dioxonaphthalene in 150 mL of ethanol that is brought to reflux. After 48 h of reflux, the reaction mixture is evaporated to dryness and purified on a flash column (support: silica; conditioning: heptane; eluent: dichloromethane) to produce 6 g of 5,6-dihydro-5,6-dioxo-11-methyl-naphtho[1',2':4,5]imidazo[1,2-a]pyridine in the form of orange crystals.

Workup

  1. temperatureto reflux
  2. temperatureAfter 48 h of reflux
  3. customthe reaction mixture is evaporated to dryness
  4. custompurified on a flash column (support: silica; conditioning: heptane; eluent: dichloromethane)

Sources & evidence

ORD record
ord-c3433ca8d1fb4f718a0d196f7c134448
Source dataset
uspto-grants-1999_11
Patent number
US05981544

Reaction notes

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