Acetic Acid → 1-(Pyridin-2-yl)cyclobutane-1-carboxylic acid

HRID 1040487Notes

Reaction equation

HRID 1040487 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([C:11]#N)[CH2:10][CH2:9][CH2:8]1.[OH2:13].CC(O)=[O:16].S(=O)(=O)(O)O>CCOCC>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([C:11]([OH:16])=[O:13])[CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 529881351-(Pyridin-2-yl)cyclobutane-1-carbonitrile

Product 1

HCID 532566591-(Pyridin-2-yl)cyclobutane-1-carboxylic acidYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Pyridin-2-yl-cyclobutanecarbonitrile (4.92 g, 31.1 mmol) was combined with water (5 mL), AcOH (5 mL) and sulfuric acid (5 mL). The homogeneous solution was heated to reflux. After 2.5 h, the solution was cooled to room temperature and poured into water (20 mL) and Et2O. The layers were separated and the Et2O layer was discarded. The aqueous layer was basified to pH 4.5-5 with 10% NaOH and extracted with DCM (2×100 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to yield 3.28 g (59%) of 1-pyridin-2-yl-cyclobutanecarboxylic acid as pale yellow solid, m/z=178.5 [M+1]+.

Workup

  1. temperatureThe homogeneous solution was heated to reflux
  2. customThe layers were separated
  3. extractionextracted with DCM (2×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-11a2597bc22f4f208b9342bd123ce593
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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