Hydrochloric Acid → 1-(Pyrazin-2-yl)cyclopropane-1-carboxylic acid

HRID 1688345Notes

Reaction equation

HRID 1688345 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1([C:10]#N)[CH2:9][CH2:8]1.[OH-:12].[Na+].Cl.C[OH:16]>>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1([C:10]([OH:16])=[O:12])[CH2:9][CH2:8]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 584311071-(Pyrazin-2-yl)cyclopropane-1-carbonitrile

Product 1

HCID 584310521-(Pyrazin-2-yl)cyclopropane-1-carboxylic acid

Conditions

Temperature
75 °C

Procedure

1-(Pyrazin-2-yl)cyclopropanecarbonitrile (0.25 g, 1.72 mmol, 1 eq) was dissolved in MeOH (5 ml) and NaOH solution (20 wt % in water, 2.0 ml) was added via syringe in one portion. The orange mixture was heated to 75° C. for 22 h., cooled to room temperature, and acidified to pH 2-3 with 6N HCl. The mixture was filtered through a pad of celite with MeOH wash and the filtrate was concentrated. The residue was suspended in ethyl acetate, dried with Na2SO4, filtered and concentrated to give the product as an orange solid. Yield: 0.18 g (64%) 1H NMR (400 MHz, DMSO-d6): δ 1.42-1.45 (m, 2H), 1.54-1.56 (m, 2H), 8.48-8.53 (m, 2H), 8.86-8.87 (d, 1H, J=1.6 Hz), 12.58 (s, 1H). LCMS: (ES+) m/z=165.2 (M+H)+

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered through a pad of celite with MeOH
  3. washwash
  4. concentrationthe filtrate was concentrated
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-761129fcdb034724a78db92aa5336ff6
Source dataset
uspto-grants-2012_04
Patent number
US08148382B2

Reaction notes

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