Sodium Hydroxide → HCID 14067394, compound

HRID 1706368Notes

Reaction equation

HRID 1706368 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8]3=[N:11][C:12]([C:14]([O:16]C)=[O:15])=[CH:13][N:7]3[C:6]=2[CH:18]=1.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8]3=[N:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][N:7]3[C:6]=2[CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14067395HCID 14067395, compound

Product 1

HCID 14067394HCID 14067394, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The methyl 8-chloro-4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylate prepared in Example 1 was suspended in 50 ml of ethanol and a solution of 1.15 g (29 mmol) of sodium hydroxide in 50 ml of water was added thereto. The mixture obtained was then heated on a steam bath until a clear solution was obtained and thin layer chromatography indicated no starting ester remaining. The solution was filtered and the filtrate was acidified while still hot to a pH of 2-3 with concentrated hydrochloric acid. On cooling, the acid crystallized out and was collected, was washed with water and dried over P2O5 under vacuum to obtain 3.20 g (97% yield) of 8-chloro-4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylic acid in the form of colorless needles with a melting point of 276°-278° C.

Workup

  1. customThe mixture obtained
  2. temperaturewas then heated on a steam bath until a clear solution
  3. customwas obtained
  4. filtrationThe solution was filtered
  5. temperatureOn cooling
  6. customthe acid crystallized out
  7. customwas collected
  8. washwas washed with water
  9. dry with materialdried over P2O5 under vacuum

Sources & evidence

ORD record
ord-265738fa6af241d8a74f9d4794d5ef2d
Source dataset
uspto-grants-1980_06
Patent number
US04207318

Reaction notes

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