Hydrazine hydrate (1:1) → HCID 59309859, compound

HRID 1513001Notes

Reaction equation

HRID 1513001 reaction equation
[Cl:1][C:2]1[C:3]([N:23]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:4][C:5]([S:9]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.O.NN>O1CCCC1.C(OCC)(=O)C>[NH2:23][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([OH:8])=[C:5]([S:9]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:4]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59309908HCID 59309908, compound

Product 1

HCID 59309859HCID 59309859, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloro-2-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)-4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)phenol (0.49 g) was dissolved in tetrahydrofuran (10 mL). To the solution was added hydrazine monohydrate (0.25 mL), and the mixture was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1) to give the title compound (0.27 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customThe insoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-ccdbf8653922484c81f115081e14e8ce
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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