4-Fluorophenol → HCID 86729560, compound

HRID 2280572Notes

Reaction equation

HRID 2280572 reaction equation
Cl[C:2]1[C:3]([C:12]([O:14]CC)=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH-].[Na+]>CN1C(=O)CCC1.Cl.O>[F:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:2]2[C:3]([C:12]([OH:14])=[O:13])=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 12283436Ethyl 3-Chloroquinoxaline-2-carboxylate

Product 1

HCID 86729560HCID 86729560, compoundYield 21.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 3-chloroquinoxaline-2-carboxylate (473.3 mg, 2.0 mmol), 4-fluorophenol (448.4 mg, 4.0 mmol) and Cs2CO3 (1.30 g, 4.0 mmol) in NMP (5 mL) was stirred at 80° C. for 16 hours. The reaction mixture was poured into water and the pH adjusted to 4 with aqueous 1N HCl. The resulting precipitate was filtered off, taken up in MeOH (3 mL). Water (0.3 mL) and NaOH (320.0 mg, 8.00 mmol) were added and the reaction mixture was stirred at 40° C. for 1 hour. The reaction mixture was diluted with 1N HCl. The resulting precipitate was filtered, washed with ether, and dried to give 3-(4-fluorophenoxy)quinoxaline-2-carboxylic acid (120 mg, 21%) as a white solid. ESI-MS m/z calc. 284.06, found 285.3 (M+1)+; Retention time: 1.29 minutes (3 minutes run).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-1507cb47e3714881883f0da584ce66fe
Source dataset
uspto-grants-2015_09
Patent number
US09139529B2

Reaction notes

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