6-Bromoquinoline → Quinoline-6-thiol

HRID 499097Notes

Reaction equation

HRID 499097 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C[S-:13].[Na+]>CC(N(C)C)=O.Cl.C(OCC)(=O)C>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([SH:13])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 792436-BromoquinolineHCID 4378561Sodium methanethiolate

Product 1

HCID 23422228Quinoline-6-thiol

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21866389Hydrogen chloride-ethyl acetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6-bromoquinoline (700 mg) in dimethylacetamide (3 ml) was added sodium thiomethoxide (1.9 g, 26.96 mmol). The mixture was heated at 150° C. for 2 hours, then cooled to ambient and diluted with 1M HCl/ethyl acetate. The organic layer was removed and the aqueous layer extracted with further ethyl acetate. The combined extracts were washed with water, then brine, dried (MgSO4), filtered and concentrated. The crude thiol (500 mg) was used directly without further purification; MS ES+, ES− 174.13

Workup

  1. temperaturecooled
  2. customThe organic layer was removed
  3. extractionthe aqueous layer extracted with further ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialbrine, dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude thiol (500 mg) was used directly without further purification

Sources & evidence

ORD record
ord-e080990acb6f49aab05404c8cad51582
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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