Sodium Carbonate → HCID 57625512, compound

HRID 2387476Notes

Reaction equation

HRID 2387476 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][N:23]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=2)[C:22](=[O:26])[CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 949565-Fluoro-2-nitrotolueneHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 57625512HCID 57625512, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-fluoro-2-nitrotoluene (1.00 g, 6.44 mmol) in DMF (6.5 mL) was added 4-benzyloxy-pyridin-2(1H)-one (1.11 g, 5.55 mmol) and Na2CO3 (0.588 g, 5.55 mmol). After stirring at 120° C. for 56 hours, the reaction mixture was cooled, and the solids were collected by filtration and washed with EtOAc (100 ml) and H2O (100 mL). The solids were triturated with hot H2O (50 mL) and then washed with Et2O (50 mL) to yield the title compound (0.94 g, 50%) as a light yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 8.08 (d, J=8.5 Hz, 1H), 7.64 (d, J=8.5 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H), 7.50 (dd, J=9.0, 2.5 Hz, 1H), 7.47-7.37 (m, 5H), 6.16 (dd, J=8.0, 3.0 Hz, 1H), 6.01 (d, J=2.5 Hz, 1H), 5.15 (s, 2H), 2.55 (s, 3H); ESI MS m/z 337 [M+H]+.

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationthe solids were collected by filtration
  3. washwashed with EtOAc (100 ml) and H2O (100 mL)
  4. customThe solids were triturated with hot H2O (50 mL)
  5. washwashed with Et2O (50 mL)

Sources & evidence

ORD record
ord-4a65866032184754ae0c745505a58dd4
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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