Acetic Acid → HCID 86683163, compound

HRID 920946Notes

Reaction equation

HRID 920946 reaction equation
[Cl:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:4]([C:8](OCC)=[O:9])[CH:5]=[N:6][CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)C.CC(=O)OCC>C1(C)C=CC=CC=1.CCCCCC>[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:8]=[O:9])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 866831643,4-Pyridinedicarboxylic acid, 5-chloro-, 3,4-diethyl ester

Product 1

HCID 86683163HCID 86683163, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a solution of diethyl 5-chloropyridine-3,4-dicarboxylate (2.43 g, 9.43 mmol) in 100 mL of toluene was added diisobutylaluminiumhydride (2.68 g, 18.86 mL, 1 molar) in hexane at −70° C. The reaction mixture was stirred for 2 h at this temperature. The reaction mixture was poured into an 5% aqueous acetic acid solution followed by the addition of EA. The phases were separated and the organic phase was washed with aq. NaHCO3 solution. The organic phase was dried and concentrated to give 2.02 g (100%) of the title compound as brown oil.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with aq. NaHCO3 solution
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9b8b3a86d3dd4f55a8c32bf62028e73a
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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