Sulfuric Acid → HCID 59265941, compound

HRID 909369Notes

Reaction equation

HRID 909369 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-ed5c98a6fb52410e9ec6c3f8e7022271
Source dataset
uspto-grants-2011_09
Patent number
US08017788B2

Reaction notes

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