Methanol → HCID 84612979, compound

HRID 527451Notes

Reaction equation

HRID 527451 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.Cl.[F:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19]N)=[CH:15][CH:14]=1.S(=O)(=O)(O)O.[CH3:26]O>>[F:12][C:13]1[CH:18]=[C:17]2[C:16](=[CH:15][CH:14]=1)[NH:19][C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:26])=[O:9])[CH2:4][C:3]2=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 1927304-Oxocyclohexanecarboxylic acid

Product 1

HCID 84612979HCID 84612979, compoundYield 100%

Conditions

Temperature
120 °C

Procedure

A stirred mixture of 96.2 mg (0.68 mmol) of 4-oxocyclohexanecarboxylic acid, 100 mg (0.62 mmol) of (4-fluorophenyl)hydrazine hydrochloride, 3 mL of methanol and 80 μL of concentrated sulfuric acid in a 5 mL microwave process vial was heated for 10 min at 120° C. under argon in a microwave. The alcoholic solution was concentrated to about one-third of the original volume and then externally cooled (ice bath). An off-white product precipitate formed, which could be filtered off and thereby was carefully washed with a little cold water. Alternatively the reaction mixture was poured onto chopped ice and water and the precipitate collected by filtration to afford the title compound in 100% yield (152 mg). C14H14FNO2, Mr=247.26; 1H NMR (400 MHz, DMSO-d6) d: 1.84-1.92 (m, 1H), 2.16-2.20 (m, 1H), 2.66-2.85 (m, 4H), 2.90 (dd, J=4.8/14.6 Hz, 1H), 3.65 (s, 3H), 6.80 (td, J=2.8/9.2 Hz, 1H), 7.10 (dd, J=2.8/10.0 Hz, 1H), 7.20 (dd, J=4.6/8.6 Hz, 1H) 10.80 (bs, 1H); LCMS (ESI) tR: 2.54 min (>99%, UV254, ELSD), m/z: 248.2 [M+1]+.

Workup

  1. concentrationThe alcoholic solution was concentrated to about one-third of the original volume
  2. temperatureexternally cooled (ice bath)
  3. customAn off-white product precipitate formed
  4. filtrationwhich could be filtered off
  5. washwas carefully washed with a little cold water
  6. additionAlternatively the reaction mixture was poured
  7. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-7f01cde2180c4d5e9ab3ba61a6e8a8d2
Source dataset
uspto-grants-2016_05
Patent number
US09346803B2

Reaction notes

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