2-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitroquinolin-4-amine → 2-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine

HRID 606103Notes

Reaction equation

HRID 606103 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH:18]=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][C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 866168892-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitroquinolin-4-amine

Product 1

HCID 866168902-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamineYield 98.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

Under a nitrogen atmosphere, acetonitrile (2 L) was added to a Parr vessel containing 5% platinum on carbon (2.0 g) and 2-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitroquinolin-4-amine (36.12 g, 90.58 mmol). The vessel was sealed, purged with nitrogen, and placed under hydrogen pressure (30 psi, 2.1×105 Pa) for 17 hours at room temperature. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting semi-solid was treated with diethyl ether, which was removed under reduced pressure to provide 33 g of 2-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine as a yellow-orange solid. A portion of the material was purified by column chromatography on silica gel (6 g, eluting with 10% ethyl acetate in hexane) to provide 0.0298 g of an analytically pure sample as pale yellow crystals, mp 127-128.0° C.

Workup

  1. customThe vessel was sealed
  2. custompurged with nitrogen
  3. customfor 17 hours
  4. customat room temperature
  5. customThe catalyst was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionThe resulting semi-solid was treated with diethyl ether, which
  8. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-0cf173aab42b4612adb2e26ff9b2661f
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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