Sulfuric Acid → 2-Methyl-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 2209508Notes

Reaction equation

HRID 2209508 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH2:5][CH2:6][CH2:7][C:8](=[O:24])[C:9]=2[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:11]=1C(O)=O.S(=O)(=O)(O)O>C(O)C>[CH3:1][C:2]1[NH:3][C:4]2[CH2:5][CH2:6][CH2:7][C:8](=[O:24])[C:9]=2[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 199589032-Methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acid

Product 1

HCID 199589342-Methyl-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinoloneYield 39.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acid (4.66 g) was suspended in ethanol (200 mL) with concentrated sulfuric acid (0.5 mL). The mixture was heated at reflux for 5 h, during which time all of the solid went into solution. The solvent was evaporated, and the residue was partitioned between aqueous 2N sodium hydroxide and ethyl acetate. The aqueous portion was extracted with ethyl acetate. The combined extracts were washed (water, brine), dried, and evaporated to yield a residue which was purified by chromatography, eluting with ethyl acetate, to afford the title compound as a pale yellow solid (1.6 g); mp 183°-185° C.; MS: 284 (M); 250 MHz NMR: 1.76 (s,3, CH3), 187 (m,2, CH2), 2.16 (m,2, CH2), 2.46 (m,2, CH2), 4.58 (d,1, J=4.9, CH), 4.64 (d,1, J=4.9, CH), 7.53 (t, 1, 7.6, Ar), 7.62 (d, 1, J=7.6, Ar), 7.96 (s,1, Ar), 7.98 (m,1, Ar), 8.80 (s,1, NH). Analysis for C16H16N2O3 :Calculated: C, 67.59; H, 5.67; N, 9.85; Found: C, 67,44; H, 5.75; 9.56.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 h, during which time all of the solid
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between aqueous 2N sodium hydroxide and ethyl acetate
  5. extractionThe aqueous portion was extracted with ethyl acetate
  6. washThe combined extracts were washed (water, brine)
  7. customdried
  8. customevaporated
  9. customto yield a residue which
  10. customwas purified by chromatography
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c5a0252001c4483ba23eebef7cf891a7
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

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