Citric Acid → HCID 67505369, compound

HRID 1929895Notes

Reaction equation

HRID 1929895 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([Br:13])[C:10]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[N:9][C:8]=1[CH3:19])C.Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Br:13][C:11]1[C:10]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[N:9][C:8]([CH3:19])=[C:7]([CH:12]=1)[C:6]([OH:20])=[O:5]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67505007HCID 67505007, compound

Product 1

HCID 67505369HCID 67505369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide solution (1 N, 3.6 mL) was added to a solution of 5-bromo-6-cyclopropylmethoxy-2-methyl-nicotinic acid ethyl ester (0.58 g, 1.8 mmol) in THF (5.3 mL). The mixture was heated for 5 h to 70° C., cooled and neutralized with hydrochloric acid (1 N, 1.8 mL). After addition of citric acid the product precipitated and was purified by chromatography on silica gel with a dichloromethane:methanol gradient to yield the title compound as colorless solid, MS (ISP) 284.1 (M−H)+.

Workup

  1. temperatureThe mixture was heated for 5 h to 70° C.
  2. temperaturecooled
  3. customprecipitated
  4. customwas purified by chromatography on silica gel with a dichloromethane

Sources & evidence

ORD record
ord-4b193fd01f75414abcb5c084176c9144
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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