Hydrochloric Acid → 7-(2,4-Dichlorophenylamino)-8-fluoro-4-methyl-cinnoline-6-carboxylic acid

HRID 500563Notes

Reaction equation

HRID 500563 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:24])[C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])[N:11]=[N:10][CH:9]=[C:8]2[CH3:25])=[O:4].[Li+].[OH-].Cl>C1COCC1.O.O>[Cl:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[NH:15][C:14]1[C:13]([F:24])=[C:12]2[C:7]([C:8]([CH3:25])=[CH:9][N:10]=[N:11]2)=[CH:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 686371297-(2,4-Dichlorophenylamino)-8-fluoro-4-methyl-cinnoline-6-carboxylic acid methyl ester

Product 1

HCID 686378117-(2,4-Dichlorophenylamino)-8-fluoro-4-methyl-cinnoline-6-carboxylic acidYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 7-(2,4-dichlorophenylamino)-8-fluoro-4-methyl-cinnoline-6-carboxylic acid methyl ester (54 mg, 0.14 mmol) in THF-water (3 mL/l mL) was added 1 N aqueous LiOH (0.30 mL, 0.30 mmol) at room temperature. After 30 minutes, the reaction mixture was adjusted to pH 6-7 with 1 N aqueous HCl, diluted with water, and extracted with EtOAc-THF. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated in vacuo to give 31 mg (60%) of the crude product (31 mg, 60%), which was used directly without further purification.

Workup

  1. extractionextracted with EtOAc-THF
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c04f5257a674d569f11cff072161cf5
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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