Sodium Hydroxide → HCID 12909299, compound

HRID 614528Notes

Reaction equation

HRID 614528 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10]3=[N:13][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][N:9]3[C:8]=2[CH:20]=1)([O-])=O.[OH-].[Na+]>C(O)(=O)C.Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10]3=[N:13][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][N:9]3[C:8]=2[CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12909298HCID 12909298, compound

Product 1

HCID 12909299HCID 12909299, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
40 °C

Procedure

5.0 g (0.018 mole) of methyl 8-nitro-4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylate were suspended in a mixture of 20 ml of acetic acid and 15 ml of concentrated hydrochloric acid and to the solution thus obtained were added 15 g (0.055 mole) of stannous chloride. The mixture obtained was stirred and warmed to 40° C. After about an hour, a crystalline product started to appear and the mixture was then cooled for two hours in an ice bath. The product (chlorostannate salt) was filtered off and washed with ether. The salt was then dissolved in water and the pH of the solution obtained was adjusted to pH 9 using dilute sodium hydroxide solution. The free amino compound was extracted with chloroform and the combined chloroform extracts were dried, filtered and evaporated. The residue was triturated with ether to obtain 2.7 g (61% yield) of methyl 8-amino-4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylate in the form of brown crystals with a melting point of 213°-4° C.

Workup

  1. customthus obtained
  2. customThe mixture obtained
  3. waitAfter about an hour
  4. temperaturethe mixture was then cooled for two hours in an ice bath
  5. filtrationThe product (chlorostannate salt) was filtered off
  6. washwashed with ether
  7. dissolutionThe salt was then dissolved in water
  8. customthe pH of the solution obtained
  9. extractionThe free amino compound was extracted with chloroform
  10. dry with materialthe combined chloroform extracts were dried
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-ce86e85794fb4edca26cc0080cbf117a
Source dataset
uspto-grants-1979_03
Patent number
US04145419

Reaction notes

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