Hydrochloric Acid → HCID 178470060, compound

HRID 336351Notes

Reaction equation

HRID 336351 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-:19])=O)=[C:6]([NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=1.CC(C)([O-])C.[K+].Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N+:17]([O-:19])=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([OH:16])=[N:8]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 53818659HCID 53818659, compound

Product 1

HCID 178470060HCID 178470060, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethyl 3-(5-chloro-2-nitrophenylamino)-3-oxopropanoate (1.5 g, 5.2 mmol) in anhydrous DMF (8 mL) was added dropwise to a solution of potassium tert-butoxide (1.2 g, 10.5 mmol) in anhydrous DMF (5 mL) at 0° C. under nitrogen, after which the mixture was stirred for 2 h. The cold mixture was diluted with water (50 mL), acidified to pH 2 with 2 N HCl 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. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (3:7), to provide 6-chloro-2-(ethoxycarbonyl)-3-hydroxyquinoxaline-1-oxide as a light yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.25 (d, 1H), 7.46 (d, 1H), 7.34 (dd, 1H), 4.55 (q, 2H), 1.45 (t, 3H) ppm; ESI MS m/z 267 [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
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with ethyl acetate/hexanes (3:7)

Sources & evidence

ORD record
ord-f3bc88f5fa7b41ab9c7f919b293ede9e
Source dataset
uspto-grants-2014_11
Patent number
US08889683B2

Reaction notes

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