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 606103ノート

反応式

HRID 606103 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0cf173aab42b4612adb2e26ff9b2661f
出典データセット
uspto-grants-2011_03
特許番号
US07915281B2

反応ノート

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