Triethylamine → Tasquinimod

HRID 367291

Reaction equation

HRID 367291 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH3:13])[N:5]([CH3:14])[C:4](=[O:15])[C:3]=1[C:16]([OH:18])=O.C(N(CC)CC)C.[F:26][C:27]([F:37])([F:36])[C:28]1[CH:35]=[CH:34][C:31]([NH:32][CH3:33])=[CH:30][CH:29]=1.S(Cl)(Cl)=O>C(Cl)Cl>[CH3:33][N:32]([C:31]1[CH:30]=[CH:29][C:28]([C:27]([F:26])([F:36])[F:37])=[CH:35][CH:34]=1)[C:16]([C:3]1[C:4](=[O:15])[N:5]([CH3:14])[C:6]2[C:11]([C:2]=1[OH:1])=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][CH:7]=2)=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 15099755N-Methyl-4-(trifluoromethyl)anilineHCID 547035823-Quinolinecarboxylic acid, 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-

Product 1

HCID 54682876TasquinimodYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To an ice-cold solution of 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid (8 g, 0.032 mol), triethylamine (15.5 ml, 0.11 mol) and 4-trifluoromethyl-N-methylaniline (6.1 g, 0.035 mol) in 150 ml of methylene chloride was added dropwise during 0.5 hours a solution of thionyl chloride (3.0 ml, 0.042 mol) in 10 ml of methylene chloride. The stirring was continued at 4° C. for 4 hours. The solution was diluted with 10 ml of methylene chloride, washed with cold 1 M sulphuric acid and then extracted with 1 M sodium hydroxide. The pH of the aqueous phase was adjusted to 8-8.5, clarified by filtration and then acidified with hydrochloric acid to pH 4. On standing a crystalline precipitate was formed which was filtered off, washed with water and dried to give the title compound (8.5 g) yield 65%.

Workup

  1. washwashed with cold 1 M sulphuric acid
  2. extractionextracted with 1 M sodium hydroxide
  3. filtrationclarified by filtration
  4. customwas formed which
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-15fa282d9460444b9289f37583f7dbea
Source dataset
uspto-grants-2000_10
Patent number
US06133285

Linked notes

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