Ethanol → N-(5-Cyano-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide

HRID 492084Notes

Reaction equation

HRID 492084 reaction equation
[C:1]([C:3]1[C:4]2[CH:5]=[CH:6][C:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:8][C:9]=2[CH2:10][CH2:11][CH:12]=1)#[N:2].CCO.[H][H]>[Pd].C(O)(=O)C>[C:1]([CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:15])=[O:16])[CH:6]=[CH:5][C:4]1=2)#[N:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 68860329N-(5-Cyano-7,8-dihydro-naphthalen-2-yl)-bezenesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 68832042N-(5-Cyano-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamideYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N-(5-Cyano-7,8-dihydro-naphthalen-2-yl)-bezenesulfonamide (5.27 g, 17.2 mmol), 70 mL EtOH, and 50 mL acetic acid were placed in a Parr vessel, and 1.0 g of 10% Palladium on carbon (Fluka Chemica Co.) was added. The reaction mixture was shaken for 15 hours under 55 psi hydrogen. The Parr vessel was purged with nitrogen and the reaction mixture was filtered. The filtrate was added to 500 mL, water, and the aqueous mixture was extracted with EtOAc. The combined organic layers were dried (MgSO4) and evaporated to yield 4.85 g (15.5 mmol, 90%) of N-(5-Cyano-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide as an oil. MS: 314 (M+H)+.

Workup

  1. additionwas added
  2. customThe Parr vessel was purged with nitrogen
  3. filtrationthe reaction mixture was filtered
  4. additionThe filtrate was added to 500 mL, water
  5. extractionthe aqueous mixture was extracted with EtOAc
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-1d3bf2e97b3d451f9e1f037106ce8e2b
Source dataset
uspto-grants-2009_05
Patent number
US07531577B2

Reaction notes

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