Hydrochloric Acid → HCID 59626030, compound

HRID 1911124Notes

Reaction equation

HRID 1911124 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59626027Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylate

Product 1

HCID 59626030HCID 59626030, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.1 g (4.0 mmol) methyl 2-(4-fluorophenyl)benzo[d]oxazole-4-carboxylate 9ee and 3.7 mL of 3N aqueous NaOH in 10 mL of THF was refluxed overnight. After cooling the reaction mixture was poured into water and acidified with conc. HCl. The resulting solid was filtered and dried to give 830 mg (79%) of 2-(4-fluorophenyl)-benzo[d]oxazole-4-carboxylic acid, 9ff. MS m/z (M+H+) 258.1.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling the reaction mixture
  3. filtrationThe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-dd6bb7fb1d90412f9d6fa9356bf2cba3
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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