Cyclopentylamine → 2-(Aminocyclopentyl)-6-chloronicotinic acid

HRID 1260592Notes

Reaction equation

HRID 1260592 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:12]1([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)(C)(C)C>[NH2:17][C:12]1([C:2]2[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 866423392-(Aminocyclopentyl)-6-chloronicotinic acidYield 29.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

15 g of 2,6-dichloronicotinic acid (70.31 mmol, Aldrich) and 34.7 ml of cyclopentylamine (351.56 mmol) are placed in a sealed tube containing 40 ml of tert-butanol. The mixture is heated at 100° C. overnight and evaporated to dryness. The residue is taken up in water and the product is acidified by pouring in an aqueous solution of acetic acid at 10%, and the mixture is then extracted with choloroform. The organic phases are combined, dried over sodium sulphate, filtered, and concentrated under vacuum. The solid residue is triturated in an ether/pentane mixture so as to give 5 g of expected product in the form of an off-white solid (yield=29.5%).

Workup

  1. customevaporated to dryness
  2. additionby pouring in an aqueous solution of acetic acid at 10%
  3. extractionthe mixture is then extracted with choloroform
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe solid residue is triturated in an ether/pentane mixture so as

Sources & evidence

ORD record
ord-eb5ec979288f40c8a2f99c0fa71282d9
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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