Hydrochloric Acid → HCID 12909281, compound

HRID 614524Notes

Reaction equation

HRID 614524 reaction equation
[CH:1]1[N:9]2[C:4]([CH2:5][O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)=[N:3][C:2]=1[C:14]([O:16]C)=[O:15].[OH-].[Na+].Cl>CO.O>[CH:1]1[N:9]2[C:4]([CH2:5][O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)=[N:3][C:2]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12909280HCID 12909280, compound

Product 1

HCID 12909281HCID 12909281, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

10.0 g (0.0435 mole) of methyl 4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylate were suspended in a mixture of 100 ml of methanol and 50 ml of water and 2N NaOH solution was added to the mixture thus obtained until the pH was 11. The mixture was warmed until the starting material had completely dissolved and thin layer chromatography indicated that no starting material remained. The solution was subsequently acidified to a pH of 2-3 with concentrated hydrochloric acid and the desired product precipitated out. After cooling, the mixture was filtered and the solid product was washed well with water. The white product was dried over P2O5 to obtain 8.5 g (91% yield) of 4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylic acid with a melting point of 256°-8° C. (decarboxylates).

Workup

  1. additionwas added to the mixture
  2. customthus obtained until the pH was 11
  3. temperatureThe mixture was warmed until the starting material
  4. dissolutionhad completely dissolved
  5. customthe desired product precipitated out
  6. temperatureAfter cooling
  7. filtrationthe mixture was filtered
  8. washthe solid product was washed well with water
  9. dry with materialThe white product was dried over P2O5

Sources & evidence

ORD record
ord-821fa31dac4c4017a7ec2ce1459b7354
Source dataset
uspto-grants-1979_03
Patent number
US04145419

Reaction notes

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