Hydrochloric Acid → 7-(4-Bromo-2-chlorophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylic acid

HRID 500569Notes

Reaction equation

HRID 500569 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]([Br:22])=[CH:18][C:17]=1[Cl:23])[N:11]=[CH:10][N:9]=[C:8]2[CH3:25])=[O:4].[Li+].[OH-].Cl>C1COCC1.O.O>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:14]2[C:13]([F:24])=[C:12]3[C:7]([C:8]([CH3:25])=[N:9][CH:10]=[N:11]3)=[CH:6][C:5]=2[C:3]([OH:4])=[O:2])=[C:17]([Cl:23])[CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 686375037-(4-Bromo-2-chlorophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylic acid methyl ester

Product 1

HCID 686372087-(4-Bromo-2-chlorophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylic acidYield 73%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 7-(4-bromo-2-chlorophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylic acid methyl ester (137 mg, 0.323 mmol) in THF-water (3 mL/l mL) was added 1 M aqueous LiOH (0.67 mL, 0.67 mmol) at room temperature. The resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was acidified to pH 6 with 1 N aqueous HCl, diluted with water, and extracted with EtOAc. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated in vacuo to give the desired product (96 mg, 73%).

Workup

  1. extractionextracted with EtOAc
  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-e8a98afc5f0349adb5a106f2f84aca04
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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