Reacción #93243

Ecuación de reacción

NaHCO3

2-aminothiophenol

4a, 5, 8, 8a-tetrahydro-1,4-naphtoquinone

HCl

→

title compound

5-Hydroxy-1,4-dihydro-12H-benzo[a]phenothiazine

Disolventes

methanol

methanol

Ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for another 2 hours
2. 2
   OtroThe organic layer was decanted
3. 3
   Otrodried
4. 4
   Otroevaporated to dryness
5. 5
   OtroThe resulting oily residue was chromatographed on silica gel (CH2Cl2)

Procedimiento

A solution of 2-aminothiophenol (385 mg) in methanol (3 ml) was added to a solution of 4a, 5, 8, 8a-tetrahydro-1,4-naphtoquinone (Ref.: Ber. 62, 2361 (1929)) (500 mg) in methanol (10 ml) and stirred for 1 hour. Then conc. HCl (2 ml) was added and the mixture was stirred for another 2 hours. Ethyl acetate was added to the reaction mixture followed by a solution of NaHCO3. The organic layer was decanted, dried and evaporated to dryness. The resulting oily residue was chromatographed on silica gel (CH2Cl2) to afford the title compound.

Fuente