Hydrochloric Acid → HCID 59626030, compound

HRID 468111Notes

Reaction equation

HRID 468111 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-cbf3194de4f743f2b7a0ea11592d5d0d
Source dataset
uspto-grants-2014_01
Patent number
US08623858B2

Reaction notes

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