HCID 18983607, compound → HCID 15479546, compound

HRID 1440430Notes

Reaction equation

HRID 1440430 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[C:7]([CH3:18])([CH3:17])[CH2:6][C:5]1=[O:19])([CH3:3])[CH3:2]>CO>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[C:7]([CH3:17])([CH3:18])[CH2:6][C:5]1=[O:19])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 18983607HCID 18983607, compound2×

Product 1

HCID 15479546HCID 15479546, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Isopropyl 4,4,-dimethyl-2-oxo-6-nitroquinoline (Compound 40, 220 mg, 0.84 mmol) was dissolved in CH3OH (3 ml). The solution was cleansed by flushing with N2 gas, and thereafter a catalytic amount of 10% Pd/C was added. The resulting mixture was hydrogenated at room temperature for 5 hours. After evaporation of the solvent the title compound was obtained in quantitative yield as a light purple oil. (184.2 mg 94%) 1H NMR d 1.23 (s, 6H), 1.49 (d, J=7.0 Hz, 6H), 2.36 (s, 2H), 4.68 (q, J=7.0 Hz, 1H), 6.55 (dd, J1=2.8 Hz, J2 =8.6 Hz, 1H), 6.64 (d, J=2.6 Hz, 1H), 6.94 (d, J=8.6 Hz, 1H).

Workup

  1. customby flushing with N2 gas
  2. additiona catalytic amount of 10% Pd/C was added
  3. customAfter evaporation of the solvent the title compound
  4. customwas obtained in quantitative yield as a light purple oil

Sources & evidence

ORD record
ord-ba81cc5af4064578bce429acf1cf09f2
Source dataset
uspto-grants-1996_03
Patent number
US05498755

Reaction notes

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