Hydrochloric Acid → 2-Amino-6-nitrophenol

HRID 2235526Notes

Reaction equation

HRID 2235526 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].[OH-].[NH4+].[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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 113122,6-DinitrophenolHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 73972Sodium sulfide nonahydrate

Product 1

HCID 51272912-Amino-6-nitrophenolYield 60.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

A suspension of 2,6-dinitrophenol 5.0 g (27 mmol), ammonium hydroxide (3 ml) and ammonium chloride 14.3 g (270 mmol) in 30 ml of water was heated to 70° C. A solution of sodium sulfide nonahydrate (24.19 g, 100 mmol) in water was added and the resulting mixture stirred at 70° C. for 2 h. The reaction was cooled to room temperature, acidified (pH 3.2) with 2N HCl, and the brown precipitate separated by filtration. The filtrate was extracted with chloroform (6×75 ml), the organic extracts combined with the precipitate, and evaporated in-vacuo to yield 2.5 g (60%) of product as a dark brown solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe brown precipitate separated by filtration
  3. extractionThe filtrate was extracted with chloroform (6×75 ml)
  4. customevaporated in-vacuo

Sources & evidence

ORD record
ord-d3044bb7ed5948238d258f47631c5975
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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