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

HRID 917391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917391
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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e7dfa14241984317bc8b999168955e75
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273878B2

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