Ethanol → Diethyl 5,8-dihydroxy-6,7-quinolinedicarboxylate

HRID 907467Notes

Reaction equation

HRID 907467 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([O:9]CC)=O)[C:2]=1[C:12]([O:14]CC)=O.[C:17]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].CC[O-].[Na+].CCO.[NH4+].[Cl-]>C1(C)C=CC=CC=1.CC(O)=O>[OH:9][C:7]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([C:17]([O:26][CH2:27][CH3:28])=[O:25])[C:12]([OH:14])=[C:2]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:1]2

Participants

8

Reactant 5

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 31249Diethyl SuccinateHCID 2723922Sodium ethoxideHCID 108895172,3-Diethyl 2,3-pyridinedicarboxylate

Product 1

HCID 135932593Diethyl 5,8-dihydroxy-6,7-quinolinedicarboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

To a mechanically stirred solution of diethyl pyridine-2,3-dicarboxylate 1 (86%, 85.6 g, 330 mmol) and diethyl succinate (70 ml, 414 mmol) in toluene (100 ml) at 95 C was added slowly a solution of NaOEt in EtOH (21%, 311 ml, 825 mmol) and this mixture was stirred at reflux o.n. It was then poured into an ice cold solution of sat NH4Cl (1.5 L) containing 60 ml AcOH. The products were extracted into EtOAc, dried over Na2SO4 and this solution was filtered through a pad of silica (400 ml) and concentrated to dryness. The residue was triturated into ether:hexane 1:2, the solid filtered, washed with hexane and air dried to yield 77.3 g (77% yield) of 2.

Workup

  1. temperatureat reflux o.n
  2. extractionThe products were extracted into EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationthis solution was filtered through a pad of silica (400 ml)
  5. concentrationconcentrated to dryness
  6. customThe residue was triturated into ether:hexane 1:2
  7. filtrationthe solid filtered
  8. washwashed with hexane and air
  9. customdried

Sources & evidence

ORD record
ord-6cb40611a8114bd1a9bd316d21907da0
Source dataset
uspto-grants-2011_09
Patent number
US08013159B2

Reaction notes

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