Hydrazine hydrate (1:1) → HCID 59309723, compound

HRID 1512988Notes

Reaction equation

HRID 1512988 reaction equation
[Cl:1][C:2]1[C:3]([N:11]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:4][C:5]([SH:10])=[C:6]([O:8][CH3:9])[CH:7]=1.O.NN>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([SH:10])=[CH:4][C:3]=1[NH2:11]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59310058HCID 59310058, compound

Product 1

HCID 59309723HCID 59309723, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-mercaptoanisole (0.65 g) in tetrahydrofuran (20 mL) was added hydrazine monohydrate (0.5 mL), and the mixture was heated at reflux for 1.5 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1) to give the title compound (0.3 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 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-2b7a1a65ef164af5b1452f02e381f2e5
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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