Tetrahydrofuran → Ethyl 4-((3-methoxyphenyl)amino)-4-oxobutanoate

HRID 513924Notes

Reaction equation

HRID 513924 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.CCN([CH2:15][CH3:16])CC.C([CH:19]([CH2:23][C:24](Cl)=[O:25])[C:20](Cl)=[O:21])C.C1C[O:30]CC1>O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:24](=[O:25])[CH2:23][CH2:19][C:20]([O:21][CH2:15][CH3:16])=[O:30])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 218646082-Ethylbutanedioyl dichloride

Product 1

HCID 14946361Ethyl 4-((3-methoxyphenyl)amino)-4-oxobutanoateYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of m-anisidine (10 g, 81.3 mmol) in THF (240 mL) was added Et3N (22 mL, 217.8 mmol) followed by ethyl succinyl chloride (11.14 g, 67.9 mmol). The reaction mixture was stirred at ambient temperature for 15 minutes. The reaction was diluted with H2O and EtOAc and the organic layer was separated. The organic layers were washed with H2O, 10% HCl (aq), sat. NaHCO3 (aq) and brine, dried over MgSO4 and concentrated under reduced pressure to give the title compound as a pale yellow solid (17.5 g, 86%). 1H NMR (400 MHz, CDCl3) δ 7.62-7.56 (m, 1H), 7.32-7.28 (m, 1H), 7.19 (t, J=8.0 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.65 (dd, J=8.2, 2.0 Hz, 1H), 4.17 (d, J=7.0 Hz, 2H), 3.80 (s, 3H), 2.81-2.70 (m, 2H), 2.70-2.60 (m, 2H), 1.26 (t, J=7.2 Hz, 3H). [M+H]=252.3.

Workup

  1. customthe organic layer was separated
  2. washThe organic layers were washed with H2O, 10% HCl (aq), sat. NaHCO3 (aq) and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b74211bddfa04021b2f5bb74e1a7e9a2
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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