Potassium Hydroxide → 5-Cyclopropylpyridine-2-carboxylic acid

HRID 627707Notes

Reaction equation

HRID 627707 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:10]([O:12]C)=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[K+]>CO>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86674749HCID 86674749, compound

Product 1

HCID 578277225-Cyclopropylpyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a reaction vial were added methyl 5-cyclopropylpicolinate (370 mg, 2.088 mmol) and potassium hydroxide (258 mg, 4.59 mmol) in MeOH (7 ml). The reaction mixture was heated to 50° C. for 1 h. It was concentrated and was treated with small amount of water, and acidified by 6N HCl until pH 2. Then the mixture was concentrated and MeOH was added. The white salt was filtered out and the filtrate was passed through silica plug to yield desired product as yellow solid which still contains some salt. It was used directly for next step. MS m/z=164.2 (M+H).

Workup

  1. concentrationIt was concentrated
  2. additionwas treated with small amount of water
  3. concentrationThen the mixture was concentrated
  4. additionMeOH was added
  5. filtrationThe white salt was filtered out

Sources & evidence

ORD record
ord-d152e07bdcb54ec3a7b6181480a274f1
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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