HCID 22643244, compound → HCID 22643230, compound

HRID 1394125Notes

Reaction equation

HRID 1394125 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[C:16]([N:18]([CH3:20])[CH3:19])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N+:21]([O-])=O)[CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[H][H]>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[C:16]([N:18]([CH3:19])[CH3:20])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH2:21])[CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 22643244HCID 22643244, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22643230HCID 22643230, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The title compound was prepared by reduction of a nitro group by catalytic hydrogenation as follows. Into a 500 mL Parr shaker bottle was placed 4.0 g of the N-[2-(3-fluorophenyl)-6-nitro-4-quinolinyl]-N,N-dimethylamine along with 150 mg of a catalyst consisting of 5% palladium on calcium carbonate support. To this was added 150 mL of ethanol, followed by application of a 50 psi hydrogen atmosphere. The reaction was shaken for 18 hr then the hydrogen atmosphere was replaced by nitrogen. The catalyst was removed by filtration, and the solution concentrated. The residue was taken up in ethyl acetate, washed with 5% sodium hydroxide solution, then the organic layer was dried over Na2SO4, filtered and concentrated. The extract was recrystallised from methylene chloride and hexane to give 2.8 g (77%) of the product.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution concentrated
  3. washwashed with 5% sodium hydroxide solution
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe extract was recrystallised from methylene chloride and hexane

Sources & evidence

ORD record
ord-a3d207c1ce244be1952eb9207d2de97e
Source dataset
uspto-grants-2008_03
Patent number
US07348340B2

Reaction notes

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