Hydrochloric Acid → 5-Cyclopropoxypyrazine-2-carboxylic acid

HRID 1754860Notes

Reaction equation

HRID 1754860 reaction equation
[OH-].[Li+].[CH:3]1([O:6][C:7]2[N:8]=[CH:9][C:10]([C:13]([O:15]C)=[O:14])=[N:11][CH:12]=2)[CH2:5][CH2:4]1.Cl>O1CCCC1.O>[CH:3]1([O:6][C:7]2[N:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[N:11][CH:12]=2)[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 117738401Methyl 5-(cyclopropoxy)pyrazine-2-carboxylate

Product 1

HCID 1177379935-Cyclopropoxypyrazine-2-carboxylic acidYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide (264 mg, 6.28 mmol) is added to a solution of methyl 5-(cyclopropoxy)pyrazine-2-carboxylate (610 mg, 3.14 mmol) in tetrahydrofuran (10 mL) and water (0.5 mL). The reaction mixture is stirred for 1 hour at 50° C., cooled to ambient temperature, diluted with water, brought to pH=2 by slow addition of 1 M HCl, and extracted with dichloromethane (4 times). The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (550 mg, 97%). ES/MS (m/e): 181.0 (M+1).

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with dichloromethane (4 times)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4b4595549d3460f92fdf10dfbcff5d2
Source dataset
uspto-grants-2015_10
Patent number
US09169271B2

Reaction notes

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