Sodium methanethiolate → 3-[(Methylsulfanyl)methyl]-2-phenylquinoline-4-carboxylic acid

HRID 2425523Notes

Reaction equation

HRID 2425523 reaction equation
Br[CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([OH:15])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.[CH3:22][S-:23].[Na+]>O1CCCC1>[CH3:22][S:23][CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([OH:15])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 234976523-(Bromomethyl)-2-phenylquinoline-4-carboxylic acid

Product 1

HCID 597997323-[(Methylsulfanyl)methyl]-2-phenylquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(Bromomethyl)-2-phenylquinoline-4-carboxylic acid (650 mg, 1.9 mmol) in tetrahydrofuran (40 mL) was added sodium methanethiolate (400 mg, 5.7 mmol). The mixture was stirred overnight, concentrated, diluted with pH 4 buffer (40 mL) and ethyl acetate (40 mL), and extracted. The organic phase was dried (MgSO4), and concentrated to afford the desired product as a brown oil which was used without purification.

Workup

  1. concentrationconcentrated
  2. additiondiluted with pH 4 buffer (40 mL) and ethyl acetate (40 mL)
  3. extractionextracted
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-531636a9dde2404fb958dbdf9102d6ad
Source dataset
uspto-grants-2011_06
Patent number
US07964733B2

Reaction notes

Loading…