Ammonia → 2-Amino-6-nitrophenol
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[OH:13])([O-:3])=[O:2].N.[Cl-].[NH4+].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].Cl>O>[NH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[OH:13]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A suspension of 2,6-dinitrophenol (5 g), ammonia (3 ml) and ammonium chloride (14.30 g) in water (30 ml) was heated to 70° C. A solution of sodium sulphide nonahydrate (24.19 g) in water (23 ml) was added and the resulting mixture stirred at 70° C. for 2 hours. The reaction was cooled to room temperature, acidified (pH 3.2) with 2N HCl, and the brown precipitate isolated by filtration. The filtrate was extracted with chloroform (6×75 ml), the organic extracts combined with the precipitate, and evaporated in-vacuo to yield a dark brown solid. The solid was purified by flash chromatography (SiO2; dichloromethane) to yield the title compound (2.86 g, 68%) as a brown solid. δH (250 MHZ;d6DMSO), 6.75 (1H,td,ArH), 6.90 (2H,bs,ArNH2), 6.92 (1H,m,ArH), 7.14 (1H,m,ArH).
Workup
- temperatureThe reaction was cooled to room temperature
- customthe brown precipitate isolated by filtration
- extractionThe filtrate was extracted with chloroform (6×75 ml)
- customevaporated in-vacuo
- customto yield a dark brown solid
- customThe solid was purified by flash chromatography (SiO2; dichloromethane)
Sources & evidence
- ORD record
- ord-42dd745f05de4a709a23ff4f9be80612
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665737
Reaction notes
Loading…