Acetic Acid → HCID 15672399, compound

HRID 1494548Notes

Reaction equation

HRID 1494548 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:3]=1[CH:16]=[O:17].C[O-].[Na+].[C:21](O)(=[O:23])C.C(Cl)Cl>CO>[CH:16]([C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][C:2]=1[O:23][CH3:21])=[O:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 10942334Sodium MethoxideHCID 15672398HCID 15672398, compound

Product 1

HCID 15672399HCID 15672399, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of dimethyl 6-chloro-5-formylpyridine-2,3-dicarboxylate (1.0 g, 0.0039 mol) in methanol (10 mL) is added to sodium methoxide (0.42 g, 0.0078 mol) in methanol (2 mL). The resulting mixture is stirred for 15 hours at 90° C. After cooling to room temperature, the reaction mixture is acidified to pH 3.0 with acetic acid. The reaction is poured into methylene chloride, washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title compound (0.62 g, 63%) as an orange oil, identified by IR and NMR spectral analyses.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-518a0b22bbd64152ab13253c6dfe51c4
Source dataset
uspto-grants-1991_06
Patent number
US05026859

Reaction notes

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