Methyl 5-chloropyrazine-2-carboxylate → 5-Chloropyrazinoic acid

HRID 1175919Notes

Reaction equation

HRID 1175919 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([Cl:11])=[CH:7][N:6]=1)=[O:4].[Cl-].[Li+].C(=O)(O)[O-].[Na+]>C(#N)C.CN(C=O)C.O>[Cl:11][C:8]1[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 433294Lithium ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 4654725-Chloropyrazinoic acidYield 61.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of methyl-5-chloropyrazine-2-carboxylate (120 mg, 0.70 mmol) in a mixture of acetonitrile (2 mL) and DMF (1 mL) was added lithium chloride (295 mg, 6.95 mmol). The suspension was heated to 160° C. for 5 mins in a Smith creator microwave after which time the reaction was diluted with water (10 mL). Saturated sodium bicarbonate solution (20 mL) was added and the aqueous layered extracted twice with ethyl acetate (30 mL). The combined organics were discarded and the aqueous layer adjusted to pH 4 with 1N hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate (20 mL) and the combined organics washed with water (2×20 mL), brine (10 mL) and dried (MgSO4). The volatiles were removed to give the title compound as a colourless solid (68 mg).

Workup

  1. extractionthe aqueous layered extracted twice with ethyl acetate (30 mL)
  2. extractionThe aqueous phase was extracted twice with ethyl acetate (20 mL)
  3. washthe combined organics washed with water (2×20 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were removed

Sources & evidence

ORD record
ord-b447858503434e169c577fca8668e624
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

Loading…