Diethyl Malonate → HCID 46916503, compound

HRID 2045938Notes

Reaction equation

HRID 2045938 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[C:18](OCC)(=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(OCC)(=O)C>[O:25]=[C:18]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 46916503HCID 46916503, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A slurry of (3-quinoxalin-2-ylphenyl)amine (200 mg, 0.904 mmol) and dietyl malonate (1.4 mL, 9.04 mmol) was heated at 160° C. in a Dean-Stark vial (Glass Solutions) for 5 hrs. The reaction mixture was diluted with ethyl acetate (25 mL), the organic phase was washed with water (20 mL) and brine (20 mL), dried over sodium sulphate, the solvent evaporated in vacuo and the residue dissolved in DCM (2 mL). The solution was loaded on a Isolute 20 g silica gel column and purified by flash chromatography (Flash Master, 5 g Isolute Silica column, gradient 0 to 5 min hexane, then ethyl acetate up to 50% over 20 min) to afford ethyl 3-oxo-3-(3-(quinoxalin-2-yl)phenylamino)propanoate (60 mg, 20% yield). LCMS calculated for C19H17N3O3 (M+H): 336.35. found 336. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.41 (1H, br.), 9.52 (1H, s), 8.52 (1H, m), 8.15-8.10 (2H, m), 8.05-8.08 (1H, m), 7.82-7.95 (3H, m), 7.55-7.60 (1H, m), 4.16 (2H, q, J=8 Hz), 3.54 (2H, s), 1.23 (3H, t, J=8 Hz).

Workup

  1. washthe organic phase was washed with water (20 mL) and brine (20 mL)
  2. dry with materialdried over sodium sulphate
  3. customthe solvent evaporated in vacuo
  4. dissolutionthe residue dissolved in DCM (2 mL)
  5. custompurified by flash chromatography (Flash Master, 5 g Isolute Silica column, gradient 0 to 5 min hexane

Sources & evidence

ORD record
ord-d12c29466c744aad8ac5d3e0befb3c2b
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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