Sodium hydride → 3-(4-nitro-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione

HRID 735244Notes

Reaction equation

HRID 735244 reaction equation
[H-].[Na+].CO[C:5](=[O:28])[C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[NH:14][C:15](=[O:27])[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[CH3:17]>C1COCC1>[Cl:12][C:11]1[CH:10]=[C:9]([Cl:13])[CH:8]=[C:7]2[C:6]=1[C:5](=[O:28])[C:16]([CH3:17])([C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)[C:15](=[O:27])[NH:14]2

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 688202774,6-Dichloro-2-(2-(4-nitro-phenyl)-propionylamino]-benzoic acid methyl ester

Product 1

HCID 115667753-(4-nitro-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dioneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (50 mg, 1.25 mmol, 60% in mineral oil) in dry THF (20 mL) was added a solution of 4,6-dichloro-2-[2-(4-nitro-phenyl)-propionylamino]-benzoic acid methyl ester (0.20 g, 0.50 mmol) in THF anhydride (5 mL) at 0° C. The reactant was stirred for 5 hours, and the reaction was quenched by addition of 0.5M HCl solution (30 mL). The resultant was extracted with ethyl acetate (50 mL×3), washed with water (50 mL×2) and brine (50 ml×2) and dried over magnesium sulfate anhydride. After evaporation of solvent, the pure objective compound (0.18 g, 99%) was obtained as pale yellow solid by a recrystallization (dichloromethane:EtOAc 3:1): 1H NMR (200 MHz, CDCl3) δ 1.79 (s, 3H, CH3), 6.80 (d, J=1.8 Hz, 1H, ArH), 7.15 (d, J=1.8 Hz, 1H, ArH), 7.38 (d, J=9.0 Hz, 2H, ArH), 8.18 (d, J=9.0 Hz, 2H), 8.43 (s, 1H, NH); MS(EI) m/e 364 [M+].

Workup

  1. customthe reaction was quenched by addition of 0.5M HCl solution (30 mL)
  2. extractionThe resultant was extracted with ethyl acetate (50 mL×3)
  3. washwashed with water (50 mL×2) and brine (50 ml×2)
  4. dry with materialdried over magnesium sulfate anhydride
  5. customAfter evaporation of solvent

Sources & evidence

ORD record
ord-8afb86db663243c2900c591f187c0b52
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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