Lithium hydroxide, monohydrate → HCID 71281774, compound

HRID 1481694Notes

Reaction equation

HRID 1481694 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.O[Li].O>C1COCC1.O>[CH3:1][N:2]([CH3:16])[C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71281789HCID 71281789, compound

Product 1

HCID 71281774HCID 71281774, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(dimethylamino)benzo[d]oxazole-6-carboxylate (2.2 g, ca. 10.0 mmol) in THF (10 mL) and H2O (10 mL) was added LiOH—H2O (1.26 g, 30.0 mmol, 3.0 eq) at room temperature. The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure then the reaction was quenched with 1N aqueous HCl (20 mL). The resulting mixture was extracted by CH2Cl2 (3×30 mL). The solvent was removed to give 2-(dimethylamino)benzo[d]oxazole-6-carboxylic acid (1.32 g, 6.4 mmol, 65%) over two steps. The crude product was used in the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe reaction was quenched with 1N aqueous HCl (20 mL)
  3. extractionThe resulting mixture was extracted by CH2Cl2 (3×30 mL)
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-c8e032bb138541a7ba3bf2877263b44a
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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