Hydrochloric Acid → Quinoline-6-thiol

HRID 500129Notes

Reaction equation

HRID 500129 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+].Cl>CN(C)C(=O)C.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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 792436-BromoquinolineHCID 4378561Sodium methanethiolate

Product 1

HCID 23422228Quinoline-6-thiol

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6-bromoquinoline (0.81 g, 3.89 mmol) in N,N-dimethylacetamide (4 mL) was added sodium methyl mercaptide (2.0 g, 28.5 mmol). The mixture was heated at 150° C. for 2 h. After cooling, the mixture was diluted with ethyl acetate, and neutralized with aqueous 1N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was directly used in the next step without further purification. (0.50 g, 79%) LCMS: (M+H)+=161.9.

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was directly used in the next step without further purification

Sources & evidence

ORD record
ord-035da4d0717a4c4b98bb7b3864f9447d
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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