Sulfuric Acid → HCID 59265941, compound

HRID 646630Notes

Reaction equation

HRID 646630 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2(O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 59265957HCID 59265957, compound

Product 1

HCID 59265941HCID 59265941, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(6-Chloro-pyridin-3-yl)cyclopentanol (2.1 g, 10.5 mmol) was treated with acetic acid (12 mL) and sulfuric acid (4 mL) and the mixture heated to reflux for 30 min. After cooling to RT, ice and 2 N NaOH (180 mL) was add and the resulting tan precipitate collected by filtration, washed with H2O and dried giving 2-chloro-5-(cyclopent-1-enyl)pyridine (1.66 g, 88%) as a tan solid: mp 59-60° C., LC/MS (ESI) m/z 179, 1H NMR (300 MHz, CDCl3) δ 8.41 (d, 1H, J=2.4 Hz), 7.66 (dd, 1H, J=8.4, 2.4 Hz), 7.25 (d, 1H, J=8.4 Hz), 6.27 (t, 1H, J=2.1 Hz), 2.69 (bm, 2H), 2.55 (bm, 2H), 2.05 (m, 2H).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 30 min
  3. filtrationthe resulting tan precipitate collected by filtration
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-b6d2ee2f993d43eca9855835867aa77f
Source dataset
uspto-grants-2010_04
Patent number
US07705156B2

Reaction notes

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