Hydrazine → (S)-2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1857610Notes

Reaction equation

HRID 1857610 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H: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]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[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][C@H: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:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 15895694HCID 15895694, compound

Product 1

HCID 54025519(S)-2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl esterYield 100.1%

Reagents, catalysts & solvents 1

HCID 16211236Trichloroiron;hexahydrateCatalyst

Procedure

To a solution of (S)-2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (Example 5, Step 5A: 750 mg in 13 mL dry methanol) was added 18 mg iron(III)chloride hexahydrate followed by 100 mg activated carbon and the mixture heated to reflux on an oil bath. After 15 minutes, hydrazine (0.169 mL) was added dropwise and the reaction allowed to proceed at reflux for 12 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 400 mL methylene chloride, washed successively with water (100 mL) and brine (100 mL), dried over sodium sulfate and concentrated in vacuo to give the title compound (crude: 710 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. temperatureat reflux for 12 hours
  4. filtrationfiltered through diatomaceous earth
  5. customthe solvent removed in vacuo
  6. washwashed successively with water (100 mL) and brine (100 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1be1ede13524de28ab7b0a8e5533839
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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