342 Mr Crocker, On the formation of Di-nitro-phenoxazines. 



The formation of Di-nitro-phenoxazines. By J. C. Crocker, 

 B.A., St John's College. 



[Read 3 February 1902.] 



In a paper by G. S. Turpin (C. S. J. 1891, 714), the use of 

 picric chloride as a reagent for the isolation and characterisation 

 of amines was recommended. It was there shewn that in the 

 case of ortho-amido-phenol, the reaction did not take the normal 

 course. The o-hydroxy-picramido derivative first formed, con- 

 densed in the presence of alkali, to a di-nitro-oxazine, with the 

 elimination of nitrous acid from the hydroxyl and picryl radicles. 

 Thus:— 



NO„ 



KOH 



-> 



NO., 



NH N0 2 



At Dr Turpin's suggestion I have investigated the generality 

 of the above reaction and the following results have been obtained 

 by the reaction of picric chloride with various orthoxy-amido- 

 compounds. in the presence of alkali. 



Eikonogen (amido-/3-naphthol sodium sulphonate). 



The substance was dissolved in dilute alcohol and treated in 

 hot solution with the calculated molecular proportions of picric 

 chloride in dilute alcohol and with alcoholic soda. Some nitrogen 

 was evolved in the reaction and from the purple-brown solution 

 formed, there separated a muddy-looking precipitate, which was 

 filtered off after cooling, and washed with water. Recrystallised 

 from hot water, in which it is only moderately soluble, the sub- 

 stance formed minute bronze plates. The sodium determination 

 shewed the body to be the expected substance, naphtho-di-nitro- 

 phenoxazine-sodium sulphonate. 



The bronze plates dried at 130° : — 



I. -2862 gm. gave "0465 Na 2 S0 4 

 II. -3048 „ -0473 

 III. -3920 „ -0606 



Na 



I. 

 5-26 



II. 

 5-03 



III. 

 5-01 



Calc. 

 5-38 



