Dimethylformamide → 6-(Cyclopentyloxy)pyridine-3-carboxylic acid

HRID 917390Notes

Reaction equation

HRID 917390 reaction equation
CN(C)C=O.Cl[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=1.[CH:16]1([OH:21])[CH2:20][CH2:19][CH2:18][CH2:17]1.[H-].[Na+]>C(O)(=O)C>[CH:16]1([O:21][C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 792226-Chloronicotinic acid

Product 1

HCID 167940206-(Cyclopentyloxy)pyridine-3-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 30 ml of N,N-dimethylformamide, 1.00 g (6.4 mmol) of 6-chloronicotinic acid and 1.72 g (20 mmol) of cyclopentanol were dissolved, followed by adding 0.80 g (20 mmol) of 60% sodium hydride, stirring at room temperature for 1 hour and heating under refluxing for 3 hours. The reaction liquid was then poured in 100 ml of ice water and acetic acid was added to make pH 5. The crystal precipitated was filtered, washed with cold water and hexane, and dried to obtain 1.06 g (yield: 80%) of 6-cyclopentyloxynicotinic acid.

Workup

  1. temperatureheating
  2. temperatureunder refluxing for 3 hours
  3. customThe reaction liquid
  4. customThe crystal precipitated
  5. filtrationwas filtered
  6. washwashed with cold water and hexane
  7. customdried

Sources & evidence

ORD record
ord-9dc371543a3a4835a7ac7cf74b39e5be
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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