Lithium hydroxide, monohydrate → 2-(3-chloro-4-fluoro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid

HRID 349500Notes

Reaction equation

HRID 349500 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=3)[NH:10][C:9]=2[C:8]([OH:22])=[CH:7][CH:6]=1)=[O:4].O[Li].O>C1COCC1.CO.O>[Cl:21][C:16]1[CH:15]=[C:14]([C:11]2[NH:10][C:9]3[C:8]([OH:22])=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=3[N:12]=2)[CH:19]=[CH:18][C:17]=1[F:20]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 691195392-(3-chloro-4-fluoro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid methyl ester

Product 1

HCID 691315522-(3-chloro-4-fluoro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acidYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Wang resin-supported 2-(3-chloro-4-fluoro-phenyl)-7-hydroxy-1H-benzoimidazole-4-carboxylic acid methyl ester (570 mg, 0.47 mmol) obtained in step 5 was dissolved in THF, LiOH.H2O (99 mg, 2.35 mmol) in MeOH—H2O was added thereto and the resulting mixture was refluxed for 5 hours. The resulting solution was cooled to room temperature and filtered. The filtrate was washed with MeOH and CH2Cl2, and dried to obtain the title compound (551 mg, 0.42 mmol) in a yield of 90%.

Workup

  1. temperaturethe resulting mixture was refluxed for 5 hours
  2. filtrationfiltered
  3. washThe filtrate was washed with MeOH and CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-301946acdb6f4de092547182bb6bffbf
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

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