Hydrazine → 2-{2-[6-Amino-3-(3-bromophenyl)-7-chloro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1857617ノート

反応式

HRID 1857617 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([N+:27]([O-])=O)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Br:38])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NN>O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([NH2:27])[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Br:38])[CH:33]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 9321HydrazineHCID 543094672-{2-[3-(3-Bromophenyl)-7-chloro-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 541646722-{2-[6-Amino-3-(3-bromophenyl)-7-chloro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester収率 76.9%

試薬・触媒・溶媒 1

HCID 16211236Trichloroiron;hexahydrate触媒

実験手順

To a solution of 2-{2-[3-(3-bromophenyl)-7-chloro-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (Example 8, 119 mg in 6 mL methanol) was added 4 mg iron(III)chloride hexahydrate followed by 25 mg activated carbon and the mixture heated to reflux on an oil bath. After 15 minutes, hydrazine (0.037 mL) was added dropwise and the reaction allowed to proceed at reflux for 3 hours. At this time, the mixture was cooled to room temperature, filtered through diatomaceous earth and the solvent removed in vacuo. The concentrate was solvated in 200 mL methylene chloride, washed successively with water (50 mL) and brine (50 mL), dried over sodium sulfate and concentrated in vacuo to give the title compound (crude: 87 mg).

後処理

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. temperatureat reflux for 3 hours
  4. filtrationfiltered through diatomaceous earth
  5. customthe solvent removed in vacuo
  6. washwashed successively with water (50 mL) and brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-79c22c481bcd408ebc83fb1bd47a884c
出典データセット
uspto-grants-2000_11
特許番号
US06147088

反応ノート

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