Hydrochloric Acid → 2-Methyl-1,3-benzoxazole-4-carboxylic acid

HRID 560310

Reaction equation

HRID 560310 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[O:16][C:15]([CH3:17])=[N:14][C:13]=12)=[O:7])C.Cl>CO>[CH3:17][C:15]1[O:16][C:12]2[C:13](=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[CH:10][CH:11]=2)[N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 593168402-Methyl-benzooxazole-4-carboxylic acid ethyl ester

Product 1

HCID 183546282-Methyl-1,3-benzoxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C. an aq. KOH solution (1.0 M, 2.40 mL) is added to a solution of 2-methyl-benzoxazole-4-carboxylic acid ethyl ester (0.98 mmol) in MeOH (5.0 mL) and stirred for 30 min. The mixture is allowed to reach RT, stirred for additional 60 min and made acidic by addition of aq. HCl (2.0 M). After removal of MeOH under reduced pressure the obtained precipitate is filtered off to give the desired product which is dried in vacuo. 1H-NMR (DMSO-d6): δ=2.64 (s, 3H); 7.41 (t, J=8.0 Hz, 1H); 7.83 (d, J=7.8 Hz, 1H); 7.88 (d, J=8.0 Hz, 1H); 12.8 (bs, 1H).

Workup

  1. customto reach RT
  2. stirringstirred for additional 60 min
  3. customAfter removal of MeOH under reduced pressure the obtained precipitate
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-3ac663708b3540fc9dc064623712b8d0
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Linked notes

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