HCID 178470060, compound → HCID 178470158, compound

HRID 336352Notes

Reaction equation

HRID 336352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N+:8]([O-])=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]([OH:18])=[N:5]2>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]([OH:18])=[N:5]2

Participants

3

Reactant 1

HCID 178470060HCID 178470060, compound

Product 1

HCID 178470158HCID 178470158, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphrous tribromide (0.36 mL) was added dropwise to a solution of 6-chloro-2-(ethoxycarbonyl)-3-hydroxyquinoxaline-1-oxide (0.50 g, 1.86 mmol) in anhydrous DMF (16 mL) at room temperature under nitrogen, after which the mixture was stirred for 12 h (at which point 1H NMR analysis of an aliquot indicated that the reaction was complete). The mixture was poured into ice-water mixture (100 mL) and extracted with methylene chloride (3×30 mL). The combined organic extracts were washed with water (45 mL), dried over sodium sulfate, filtered and the solvents were removed under reduced pressure to provide 6-chloro-2-(ethoxycarbonyl)-3-hydroxyquinoxaline as a light yellow solid that was suitable for use without further purification: 1H NMR (400 MHz, CDCl3) δ 7.89 (d, 1H), 7.48 (d, 1H), 7.37 (dd, 1H), 4.54 (q, 2H), 1.48 (t, 3H) ppm; ESI MS m/z 251 [M−H]−.

Workup

  1. extractionextracted with methylene chloride (3×30 mL)
  2. washThe combined organic extracts were washed with water (45 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-a4338ea6aa4b41e2badd1e59e3272454
Source dataset
uspto-grants-2014_11
Patent number
US08889683B2

Reaction notes

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