Dichloromethane → HCID 54719507, compound

HRID 1937437Notes

Reaction equation

HRID 1937437 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:17])=[C:5]([C:14]([OH:16])=O)[C:6](=[O:13])[N:7]2[CH3:12].C([N:20]([CH2:23][CH3:24])[CH2:21]C)C.S(Cl)(Cl)=O.[CH2:29]([Cl:31])Cl>>[C:2]1([C:11]2[CH:2]=[CH:3][C:8]([N:7]([CH3:12])[C:6]([C:5]3[C:14](=[O:16])[N:20]([CH3:21])[C:23]4[C:24]([C:4]=3[OH:17])=[C:29]([Cl:31])[CH:6]=[CH:5][CH:4]=4)=[O:13])=[CH:9][CH:10]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:3]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 547202275-Chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Product 1

HCID 54719507HCID 54719507, compound

Procedure

To an ice-cold solution of 5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxylic acid (1.6 g, 6.5 mmol), triethylamine (3 ml, 22.7 mmol), N-metyl-4-aminodiphenyl (1.3 g, 7 mmol) in methylene chloride (25 ml) was added dropwise during 10 minutes a solution of thionyl chloride (1.0 g, 8.4 mmol) in methylene chloride (10 ml). Stirring was continued at 4° C. for 4 hours. The solution was diluted with methylene chloride (10 ml), 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 further acidified with hydrochloric acid solution to pH 4. After standing a crystalline precipitate was formed and was filtered off, washed with water and dried to give the title compound (1.9 g).

Workup

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

Sources & evidence

ORD record
ord-168a22b5234b438895fa793307153898
Source dataset
uspto-grants-2002_05
Patent number
US06395750B1

Reaction notes

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