Reaction #1354119

Reaction equation

3-(N,N-diethylamino)phenol

3,5-dichloro-2-hydrazinopyridine

hydrogen peroxide water

iodine

→

2-(3,5-dichloro-2-pyridylazo)-5-(diethylamino)phenol

Solvents

acetic acid

dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONwere mixed
2. 2
   workup.STIRRINGthe mixture was stirred overnight
3. 3
   FiltrationThe reaction mixture was filtrated
4. 4
   workup.ADDITIONether and water were added to the filtrate
5. 5
   workup.STIRRINGby stirring
6. 6
   workup.STIRRINGAfter stirring
7. 7
   Otherthe ether layer was collected
8. 8
   Othercondensed
9. 9
   Otherto precipitate crystals
10. 10
    FiltrationThe crystals were filtrated for collection
11. 11
    Otherdried
12. 12
    Otherto give

Procedure

Next, a flask was loaded with 3-(N,N-diethylamino)phenol (1.7 g), dimethylformamide (14 ml), acetic acid (5 ml) and iodine (0.24 g), and they were mixed, followed by addition of 3,5-dichloro-2-hydrazinopyridine (1.6 g) to the flask with stirring. Then, to this, a 30% hydrogen peroxide water (2.4 g) was dropwise added in 90 minutes and the mixture was stirred overnight. The reaction mixture was filtrated, and ether and water were added to the filtrate, followed by stirring. After stirring, the ether layer was collected and condensed to precipitate crystals. The crystals were filtrated for collection and dried to give intended crystals (0.54 g).

Source