HCID 57263972, compound → HCID 22648286, compound

HRID 1838816Notes

Reaction equation

HRID 1838816 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[S:10][C:11]3[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N:14]=[CH:13][C:12]=3[N:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].C(O)(=O)C>[C:1]1([CH2:7][CH2:8][C:9]2[S:10][C:11]3[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N:14]=[CH:13][C:12]=3[N:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 57263972HCID 57263972, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22648286HCID 22648286, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A small amount of catalyst (5% palladium on activated carbon) was added to a suspension of 2-(2-phenyl-1-ethenyl)thiazolo[4,5-c]quinoline (1.16 g, Example 21 Part B) in acetic acid (200 mL). The mixture was reduced on a Parr apparatus under a 50 psi (3.5 Kg/cm2) hydrogen atmosphere for 1 day. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under vacuum. The residue was dissolved in dichloromethane, washed with sodium bicarbonate then with water, dried over magnesium sulfate and then concentrated under vacuum to provide 0.88 g of 2-(2-phenyl-1-ethyl)thiazolo[4,5-c]quinoline as an oily solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with sodium bicarbonate
  6. dry with materialwith water, dried over magnesium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d98bae9dc9424718b867c6098d7809d9
Source dataset
uspto-grants-2004_01
Patent number
US06677334B2

Reaction notes

Loading…