Ethyl-alpha-carbethoxy-4-methylamino-2-nitrodihydrocinnamate → 7-Methylamino-3-carbethoxy-3,4-dihydro-2-quinolone

HRID 414700Notes

Reaction equation

HRID 414700 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:18](OCC)=[O:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH3:14])=[CH:9][C:8]=1[N+:15]([O-])=O)[CH3:2].[H][H]>[Pd].O1CCOCC1>[CH3:14][NH:13][C:10]1[CH:9]=[C:8]2[C:7]([CH2:6][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:23])[C:18](=[O:19])[NH:15]2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 21280186Ethyl-alpha-carbethoxy-4-methylamino-2-nitrodihydrocinnamateHCID 178418361HCID 178418361, compound

Product 1

HCID 212801857-Methylamino-3-carbethoxy-3,4-dihydro-2-quinoloneYield 25.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2.6 g of the diester (4), of 10% Pd on charcoal and 75 mL of dioxane were shaken under 50 psi of hydrogen for 17 hours at 50° C. The catalyst was removed by filtering through Celite and the solvent was removed. The residue was chromatographed on 200 g of silica gel eluting with 3:17 (v/v) acetone: CH2Cl2. Fractions 75-120 (17 mL/fraction) were combined and concentrated to yield 0.5 g of a white powder. Recrystallization from MeOH-H2O produced an analytical sample, m.p. 171°-172° C.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through Celite
  3. customthe solvent was removed
  4. customThe residue was chromatographed on 200 g of silica gel eluting with 3:17 (v/v) acetone
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-88e5208a9caa4a1a9f10148813efb15d
Source dataset
uspto-grants-1988_12
Patent number
US04794079

Reaction notes

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