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

HRID 882791

Reaction equation

HRID 882791 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 (1.0M, 2.40 mL) is added to a solution of 2-methyl-benzooxazole-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. hydrochloric acid (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-bd690755fa9d4336a93624b3eb6a4a31
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Linked notes

Loading…