Propionyl chloride → HCID 952076, compound

HRID 2045916Notes

Reaction equation

HRID 2045916 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.CCN(C(C)C)C(C)C.[C:27](Cl)(=[O:30])[CH2:28][CH3:29]>C1COCC1.C(OCC)(=O)C>[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]([NH:17][C:27](=[O:30])[CH2:28][CH3:29])[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 952076HCID 952076, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (200 mg, 0.904 mmol) and DIEA (180 μL, 1.09 mmol) in THF (5 mL), propionyl chloride (87 μL, 1.0 mmol) was added and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate (20 mL), the organic phase was washed with water (10 mL), brine (10 mL), dried over MgSO4, and the solvent evaporated in vacuo. The resulting solid was triturated with diethyl ether and dried to afford 170 mg (67%) N-[3-(quinoxalin-2-yl)phenyl]propionamide. LCMS calculated for C17H15N3O (M+H): 278.12. found 276.00. 1H-NMR (CDCl3, 400 Mhz) δH: 9.44 (1H, br. s), 8.32 (1H, s), 8.14 (m, 2H), 7.41 (1H, d, J=7.5 Hz), 7.88-7.55 (4H, m), 7.52 (m, 1H), 7.40 (1H, br. S), 2.45 (2H, q, J=7 Hz), 1.28 (3H, t, J=7 Hz).

Workup

  1. washthe organic phase was washed with water (10 mL), brine (10 mL)
  2. dry with materialdried over MgSO4
  3. customthe solvent evaporated in vacuo
  4. customThe resulting solid was triturated with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-060beb4e455d45beb8f1cba9dc3b5143
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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