Acetic Acid → 1-(5-Iodopyridin-2-YL)cyclobutanecarboxylic acid

HRID 2038756Notes

Reaction equation

HRID 2038756 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[OH2:14].CC(O)=[O:17].S(=O)(=O)(O)O>CCOCC>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]([OH:17])=[O:14])[CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 708006921-(5-Iodopyridin-2-YL)cyclobutanecarbonitrile

Product 1

HCID 675084441-(5-Iodopyridin-2-YL)cyclobutanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
115 °C

Procedure

1-(5-Iodo-pyridin-2-yl)-cyclobutane carbonitrile (4.0 g, 14 mmol) was combined with water (5.0 mL), glacial AcOH (5.0 mL) and concentrated sulfuric acid (5.0 mL). The homogeneous solution was heated to reflux (external bath: 115° C.). After 5 h, the solution was cooled to room temperature and poured into water (10 mL) and Et2O (15 mL). The layers were separated and the Et2O layer was discarded. The aqueous layer was adjusted to pH 4.5-5 by the addition of 2M aq. NaOH and then extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 layers were washed with brine, dried over MgSO4, filtered and concentrated to yield 3.92 g of 1-(5-iodo-pyridin-2-yl)-cyclobutane carboxylic acid, m/z 304.4 [M+H]+.

Workup

  1. temperatureThe homogeneous solution was heated
  2. temperaturethe solution was cooled to room temperature
  3. customThe layers were separated
  4. additionThe aqueous layer was adjusted to pH 4.5-5 by the addition of 2M aq. NaOH
  5. extractionextracted with CH2Cl2 (3×50 mL)
  6. washThe combined CH2Cl2 layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6887ef12d60e4083bf32d557f34e150d
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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