Hydrochloric Acid → 2H-1,4-Benzoxazine

HRID 1856454Notes

Reaction equation

HRID 1856454 reaction equation
C([BH3-])#N.[Na+].[CH2:5]1[N:10]2C3CCNCC=3[C:13]3=[CH:14][CH:15]=[CH:16][C:8](=[C:9]23)[O:7][CH2:6]1.Cl.[OH-].[Na+]>FC(F)(F)C(O)=O>[O:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[N:10]=[CH:5][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 20304687HCID 20304687, compound

Product 1

HCID 152462522H-1,4-Benzoxazine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Powdered sodium cyanoborohydride (25 g) is added, in small portions, to a well-stirred and cooled (5°) solution of 1,2,7,8,9,10-hexahydropyrido[3', 4': 4,5]pyrrolo[1,2,3-de][1,4]benzoxazine (20 g) in trifluoroacetic acid (250 ml) at such a rate that excessive frothing is avoided. After the addition is complete, the mixture is stirred at room temperature for 2 hours, treated with 6N hydrochloric acid (150 ml), and refluxed for 30 minutes. It is then cooled and basified with 25% sodium hydroxide and extracted thrice with chloroform. The combined chloroform extracts are washed thoroughly with water, dried over magnesium sulfate, and stripped of the solvent under reduced pressure to furnish a crystalline solid which is recrystallized from hexane to yield the title compound, m.p. 112°-113°.

Workup

  1. additionAfter the addition
  2. stirringthe mixture is stirred at room temperature for 2 hours
  3. temperaturerefluxed for 30 minutes
  4. temperatureIt is then cooled
  5. extractionextracted thrice with chloroform
  6. washThe combined chloroform extracts are washed thoroughly with water
  7. dry with materialdried over magnesium sulfate
  8. customto furnish a crystalline solid which
  9. customis recrystallized from hexane

Sources & evidence

ORD record
ord-7bd03f61370440c596e8030a0f92b768
Source dataset
uspto-grants-1980_08
Patent number
US04219550

Reaction notes

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