Ethanol → Ethyl 2-chloro-6-methoxyisonicotinate

HRID 1908830Notes

Reaction equation

HRID 1908830 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:16][CH3:17])[N:15]=1)[C:10]([OH:12])=[O:11].C([O-])(O)=O.[Na+].[CH2:23](O)[CH3:24]>>[CH2:23]([O:11][C:10](=[O:12])[C:9]1[CH:13]=[C:14]([O:16][CH3:17])[N:15]=[C:7]([Cl:6])[CH:8]=1)[CH3:24]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 27821242-Chloro-6-methoxypyridine-4-carboxylic acid

Product 1

HCID 13611989Ethyl 2-chloro-6-methoxyisonicotinate

Conditions

Temperature
70 °C

Procedure

Sulfuric acid (1 mL) is added to a suspension of 2-chloro-6-methoxy-isonicotinic acid (4.16 g, 22.2 mmol) in ethanol (20 mL). The clear solution is stirred at 70° C. for 18 h. The mixture is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3×250 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give 2-chloro-6-methoxy-isonicotinic acid ethyl ester (4.32 g) as a white solid; LC-MS: tR=1.00 min, [M+1]+=215.89.

Workup

  1. extractionextracted three times with EA (3×250 mL)
  2. dry with materialextracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried

Sources & evidence

ORD record
ord-f4ba791d6f6945f695696b19cedefeeb
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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