Hydrochloric Acid → 3-(4-nitro-phenyl)-7-chloro-3-methyl-1H-quinoline-2,4-dione

HRID 735262Notes

Reaction equation

HRID 735262 reaction equation
[H-].[Na+].C[O:4][C:5](=O)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[NH:13][C:14](=[O:26])[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[CH3:16].Cl>CN(C=O)C>[Cl:12][C:9]1[CH:8]=[C:7]2[C:6]([C:5](=[O:4])[C:15]([CH3:16])([C:17]3[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=3)[C:14](=[O:26])[NH:13]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 68815880HCID 68815880, compound

Product 1

HCID 116169013-(4-nitro-phenyl)-7-chloro-3-methyl-1H-quinoline-2,4-dioneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of a sodium hydride (1.5 g, 37.5 mmol, 60% in mineral oil) in dry DMF (50 mL) was added a solution of 4-chloro-2-[2-(4-nitro-phenyl)-propionyl amino]-benzoic acid methyl ester (6.4 g, 17.5 mmol) in dry DMF (20 mL) at 0° C. The reaction mixture was stirred for 30 minutes, and the reaction was qeunched by the addition of 0.5M HCl solution (100 mL). The resulting mixture was extracted with ethyl acetate (200 mL×3). The organic layer was washed with water (200 ml×2) and brine (200 ml×2), and dried over anhydrous MgSO4. After evaporation fo the solvent, the residue was purified by a flash column chromatography (n-hexane:EtOAc=5:1) to provide the objective compound (5.50 g, 95%) as pale yellow solid: 1H NMR (200 MHz, CDCl3) δ 1.93 (s, 3H, CH3), 7.00 (d, J=1.8 Hz, 1H, ArH), 7.14 (dd, J=8.4, 2.0 Hz, 1H, ArH), 7.49 (d, J=9.2 Hz, 2H, ArH), 8.18 (d, J=9.2 Hz, 2H, ArH), 11.25 (br, 1H, NH); m.p. 209-210° C.; MS(EI) m/e 330 [M+].

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (200 mL×3)
  2. washThe organic layer was washed with water (200 ml×2) and brine (200 ml×2)
  3. dry with materialdried over anhydrous MgSO4
  4. customAfter evaporation
  5. customthe residue was purified by a flash column chromatography (n-hexane:EtOAc=5:1)

Sources & evidence

ORD record
ord-41fc36806a954db087450ec3b2d17674
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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