Ethanol → 4-[3-(2-Hydrazino-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075689Notes

Reaction equation

HRID 2075689 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12][C:13]3[CH:14]=[C:15]([C:19]4([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:3]=1.CCO.O.[NH2:31][NH2:32]>>[NH:31]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12][C:13]3[CH:14]=[C:15]([C:19]4([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:3]=1)[NH2:32]

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 582577564-[3-(2-Chloro-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 582577744-[3-(2-Hydrazino-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Procedure

5h (4.4 g, 11.6 mmol) was suspended in hydrazine hydrate (11 mL) and EtOH (45 mL) and heated to 80° C. overnight. The reaction was cooled to room temperature and concentrated, and then diluted with EtOAc and water. The aqueous layer was extracted with EtOAc twice, and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was dissolved in CH2Cl2 (15 mL) and heated to dissolve as much of the material as possible. Hexanes (45 mL) was added slowly, and the mixture was stirred for 30 minutes. The precipitate was filtered, rinsed with hexanes, and dried to give the desired product, 5i.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in CH2Cl2 (15 mL)
  9. temperatureheated
  10. dissolutionto dissolve as much of the material as possible
  11. additionHexanes (45 mL) was added slowly
  12. filtrationThe precipitate was filtered
  13. washrinsed with hexanes
  14. customdried

Sources & evidence

ORD record
ord-edb82dfe87f342faacc2c2767cafc08d
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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