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

HRID 1040475Notes

Reaction equation

HRID 1040475 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 (849 mg, 5.85 mmol) was dissolved in MeOH (7 mL) and NaOH solution (20 wt % in water, 2.0 mL, 10 mmol) 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 using MeOH and the filtrate was concentrated. The residue was suspended in EtOAc, dried with Na2SO4, filtered and concentrated to give 111 mg of the title compound as an orange solid, m/z 165.28 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-d6e9b4286c3243798c42fccfc54f0ca6
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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