Sodium Acetate → 2-Oxo-2-(3-(quinoxalin-2-yl)phenylamino)ethyl acetate

HRID 2045935Notes

Reaction equation

HRID 2045935 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)=[O:4].[C:22]([O-:25])(=[O:24])[CH3:23].[Na+]>C(#N)C.C(OCC)(=O)C>[C:22]([O:25][CH2:2][C:3](=[O:4])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 46916455HCID 46916455, compound

Product 1

HCID 469164592-Oxo-2-(3-(quinoxalin-2-yl)phenylamino)ethyl acetateYield 74.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-N-(3-(quinoxalin-2-yl)phenyl)acetamide (100 mg, 0.292 mmol) and sodium acetate (159 mg, 1.168 mmol) in acetonitrile (5 mL) was heated in microwave at 140° C. for 7.5 min. The dark-yellow solution was diluted with ethyl acetate (25 mL), washed with water (20 mL), dried over sodium sulphate and the solvent evaporated to afford 2-oxo-2-(3-(quinoxalin-2-yl)phenylamino)ethyl acetate (70 mg, 74% yield). LCMS calculated for C18H15N3O3 (M+H): 322.33. found 322. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.3 (1H, br.), 9.51 (1H, s), 8.52 (1H, m), 8.15-8.20 (2H, m), 8.08-8.10 (1H, m), 7.82-8.00 (3H, m), 7.55-7.60 (1H, m), 4.70 (2H, s), 2.15 (3H, s).

Workup

  1. washwashed with water (20 mL)
  2. dry with materialdried over sodium sulphate
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-db5af4a80aef463b95772323999b74ef
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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