Dimethylformamide → 6-(Cyclohexyloxy)-3-pyridinecarboxylic acid

HRID 917391Notes

Reaction equation

HRID 917391 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:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[H-].[Na+]>C(O)(=O)C>[CH:16]1([O:22][C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 792226-Chloronicotinic acid

Product 1

HCID 167944166-(Cyclohexyloxy)-3-pyridinecarboxylic acidYield 92%

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 2.00 g (20 mmol) of cyclohexanol 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 1.30 g (yield: 92%) of 6-cyclohexyloxynicotinic 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-e7dfa14241984317bc8b999168955e75
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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