Hydrochloric Acid → 5-Chloro-6-(cyclopropylmethoxy)pyridine-3-carboxylic acid

HRID 2277175Notes

Reaction equation

HRID 2277175 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].C1COCC1.[OH-].[Li+].Cl>CO>[Cl:1][C:2]1[C:3]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86731230Methyl 5-chloro-6-(cyclopropylmethoxy)nicotinate

Product 1

HCID 284139575-Chloro-6-(cyclopropylmethoxy)pyridine-3-carboxylic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 5-chloro-6-(cyclopropylmethoxy)nicotinate (2.00 g), THF (15 mL), methanol (1.7 mL) and 2 M aqueous lithium hydroxide solution (8.3 mL) was stirred at room temperature for 20 min. The reaction mixture was neutralized with 1 M hydrochloric acid at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure, and the obtained solid was washed with diethyl ether/hexane to give the title compound (1.68 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washthe obtained solid was washed with diethyl ether/hexane

Sources & evidence

ORD record
ord-a3fdfb6170fb479a95681a75a9c1f3ce
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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