Hydrochloric Acid → HCID 58933648, compound

HRID 854295Notes

Reaction equation

HRID 854295 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[C:7](C=O)[CH:6]=1)[CH3:2].[CH:14]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])OCC.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:6]=[CH:7][N:8]=[C:9]([CH:14]([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23])[CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 31214Ethyl orthoformateHCID 19600808Ethyl 2-formylpyridine-4-carboxylate

Product 1

HCID 58933648HCID 58933648, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
110 °C

Procedure

To a solution of 2-formyl-isonicotinic acid ethyl ester (5.0 g, 0.027 mol) in ethanol (9 mL) was added triethyl orthoformate (6.2 mL, 0.037 mol) followed by a solution of 6N hydrochloric acid in ethanol (1.5 mL). The mixture was heated to 110° C. (reflux) for 1.5 h, cooled to rt and solid potassium carbonate (1.80 g) added. The mixture was stirred for 5 min, concentrated in vacuo, and redissolved in diethyl ether (100 mL). The reaction was filtered through silica and the resulting cake washed with diethyl ether (50 mL). The filtrated was concentrated in vacuo to give 2-diethoxymethyl-isonicotinic acid ethyl ester as an oil.

Workup

  1. temperature(reflux) for 1.5 h
  2. temperaturecooled to rt
  3. concentrationconcentrated in vacuo
  4. dissolutionredissolved in diethyl ether (100 mL)
  5. filtrationThe reaction was filtered through silica
  6. washthe resulting cake washed with diethyl ether (50 mL)
  7. concentrationThe filtrated was concentrated in vacuo

Sources & evidence

ORD record
ord-35c7d8501b4a40da83f010235aa1b3b6
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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