Hydrochloric Acid → 2-Methyl-1,3-benzoxazole-6-carboxylic acid

HRID 1907708Notes

Reaction equation

HRID 1907708 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11]([O:13]C)=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.CO.[OH-].[K+].Cl>C1COCC1.O>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 12157467Methyl 2-methylbenzo[d]oxazole-6-carboxylate

Product 1

HCID 184756892-Methyl-1,3-benzoxazole-6-carboxylic acidYield 110.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of compound 138 (920 mg, 4.815 mmol) in THF:MeOH (30 mL of a 1:1 solution) was treated with a solution of potassium hydroxide (0.698 g, 17.86 mmol) in H2O (15 mL). The reaction mixture was stirred for 65 min at room temperature then quenched with 1N HCl (18 mL, 18.6 mmol) (final pH of 2.5), THF was removed under reduced pressure and the remaining aqueous solution was cooled to −78° C. and lyophilized to give compound 139 (940 mg, quantitative).

Workup

  1. customwas removed under reduced pressure
  2. temperaturethe remaining aqueous solution was cooled to −78° C.

Sources & evidence

ORD record
ord-e3a548074533478da9bed1435ef0b6a5
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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