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 1857617Notes

Reaction equation

HRID 1857617 reaction equation
[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]

Participants

4

Reactant 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

Product 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 esterYield 76.9%

Reagents, catalysts & solvents 1

HCID 16211236Trichloroiron;hexahydrateCatalyst

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-79c22c481bcd408ebc83fb1bd47a884c
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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