Cyclopentanol → HCID 22145838, compound

HRID 993287Notes

Reaction equation

HRID 993287 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[CH:13]1([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14]1>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:18][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12]

Participants

3

Reactant 2

HCID 7298CyclopentanolHCID 22145673HCID 22145673, compound

Product 1

HCID 22145838HCID 22145838, compound

Procedure

6-Chloro-5-methoxypyridine-2-carbonyl chloride (5.8 g) is added to dry cyclopentanol (50 mL) and the mixture refluxed for 4 hours. The mixture is concentrated, the residue dissolved in ethyl acetate (400 mL) and the ethyl acetate solution is washed with water (3×250 mL). After drying (MgSO4) the solution is evaporated to dryness to give cyclopentyl 6-chloro-5-methoxypyridine-2-carboxylate (6.3 g) as a buff solid, m.p. 90-92° C. [Elemental analysis: C, 55.9; H, 5.47; Cl, 13.9; N, 5.48%. calculated: C, 56.36; H, 5.52; Cl, 13.8; N, 5.48%.].

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. concentrationThe mixture is concentrated
  3. dissolutionthe residue dissolved in ethyl acetate (400 mL)
  4. washthe ethyl acetate solution is washed with water (3×250 mL)
  5. dry with materialAfter drying (MgSO4) the solution
  6. customis evaporated to dryness

Sources & evidence

ORD record
ord-2a64b404ffee471ab5b442cab7456501
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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