HCID 86616895, compound → HCID 86616896, compound

HRID 606118Notes

Reaction equation

HRID 606118 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][CH2:17][C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH:19]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>[Pt].C(#N)C>[Cl:1][C:2]1[C:11]([NH2:12])=[C:10]([NH:15][CH2:16][CH2:17][C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH:19]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 86616895HCID 86616895, compound

Product 1

HCID 86616896HCID 86616896, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent2×

Procedure

Under a nitrogen atmosphere, acetonitrile (1.5 L) was added to a Parr vessel containing 5% platinum on carbon (1.5 g), which had been wet with a small amount of acetonitrile, and 2-chloro-N-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}-3-nitroquinolin-4-amine (23.20 g, 56.20 mmol). The vessel was sealed, purged three times with hydrogen, and placed under hydrogen pressure (30 psi, 2.1×105 Pa) for 18 hours at room temperature. The catalyst was removed by filtration, and the majority of the filtrate was concentrated under reduced pressure. A solid was present in the remaining filtrate and was isolated by filtration to provide 11.3 g of 2-chloro-N4-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}quinoline-3,4-diamine as a yellow solid.

Workup

  1. customThe vessel was sealed
  2. custompurged three times with hydrogen
  3. customfor 18 hours
  4. customat room temperature
  5. customThe catalyst was removed by filtration
  6. concentrationthe majority of the filtrate was concentrated under reduced pressure
  7. customwas isolated by filtration

Sources & evidence

ORD record
ord-346eef8ef45544a18cac5a37b0d6a0bd
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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