Water → HCID 58328048, compound

HRID 869685Notes

Reaction equation

HRID 869685 reaction equation
[CH2:1](/[C:3](/[N:9]=N/C(OC(C)(C)C)=O)=[CH:4]\[C:5]([O:7][CH3:8])=[O:6])[CH3:2].[C:18]1([NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1N.O.O1CCC[CH2:28]1>>[CH2:1]([C:3]1[C:4]([C:5]([O:7][CH2:8][CH3:28])=[O:6])=[N:25][C:18]2[C:23]([N:9]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 7243O-PhenylenediamineHCID 8028TetrahydrofuranHCID 178447579HCID 178447579, compound

Product 1

HCID 58328048HCID 58328048, compound

Procedure

Preparation was performed in a similar manner as Example 1.001 (a). To a solution of tert-butyl (E)-[(1E)-1-ethyl-3-methoxy-3-oxoprop-1-en-1-yl]diazenecarboxylate (see Synlett. 2003, 8, 1183; 1.50 g, 6.19 mmol) in tetrahydrofuran (30 mL) was added 1,2-phenylenediamine (683 mg, 6.19 mmol) at room temperature. After being stirred for 22 hour, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was combined and dried over magnesium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=6:1) to give ethyl 3-ethylquinoxaline-2-carboxylate. MS (APCI): m/z 217 (M+H).

Workup

  1. customPreparation
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-37e34b2034614a9e89394bc39acccbf7
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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