Hydrochloric Acid → HCID 54724213, compound

HRID 1866931Notes

Reaction equation

HRID 1866931 reaction equation
[H-].[Na+].C(S)C.[F:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[CH2:10][N:11]1[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]([C:19]#[N:20])[C:12]1=[O:21].Cl>CN(C=O)C>[F:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[CH2:10][N:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([C:19]#[N:20])[C:12]1=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 22050432HCID 22050432, compound

Product 1

HCID 54724213HCID 54724213, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of sodium hydride (92 mg of a 60% dispersion in mineral oil, 2.3 mmol) in DMF (7 mL) was added ethanethiol (0.14 g, 2.2 mmol), followed by a solution of 1-(3-fluorobenzyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (0.23 g, 0.89 mmol) in DMF (2 mL), and the reaction mixture was heated to 100° C. The reaction mixture was cooled to room temperature, acidified with 3 N HCl, and washed with EtOAc. The organic solution was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to give 1-(3-fluorobenzyl)-4-hydroxy-2-oxo-1,2-dihydro-pyridine-3-carbonitrile as an off-white solid (0.20 g, 91%): 1H NMR (300 MHz, MeOD) δ 8.00 (s, 1H), 7.82 (d, J=8 Hz, 1H), 7.40-7.30 (m, 1H), 7.15-7.00 (m, 2H), 6.13 (d, J=8 Hz, 1H), 5.11 (s, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with EtOAc
  3. washThe organic solution was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d026309e338443c9857740daa8876574
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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