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ChemicalBook CAS DataBase List 2-Chloro-5-aminophenol
6358-06-1

2-Chloro-5-aminophenol synthesis

5synthesis methods
2-Chloro-5-nitrophenol

619-10-3

2-Chloro-5-aminophenol

6358-06-1

Step 1: 2-Chloro-5-nitrophenol (20.0 g, 115.2 mmol) was dissolved in a solvent mixture of ethanol (150 mL) and water (150 mL). To this solution, iron powder (32.2 g, 576.2 mmol) and ammonium chloride (32.1 g, 599.3 mmol) were added sequentially. The reaction mixture was heated to reflux and kept for 2 hours. After completion of the reaction, it was cooled to room temperature and filtered to remove insoluble material. The filtrate was concentrated to dryness under reduced pressure. The residue was purified by fast column chromatography (eluent: hexane/ethyl acetate = 9:1) to afford 5-amino-2-chlorophenol (15.85 g, 96% yield) as a white solid.

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Yield:6358-06-1 98%

Reaction Conditions:

Pt/C in ethyl acetate

Steps:

1.b b).
b). 2-Chloro-5-aminophenol A solution of 2-chloro-5-nitrophenol (25 g, 0.14 mol) in ethyl acetate (150 mL) was treated with 5% Pt/C (250 mg) and the mixture shaken under a hydrogen atmosphere (30 psi) for 4 h. The mixture was filtered through Celiteg and the residue washed well with hot ethyl acetate. The filtrate was treated with activated charcoal and re-filtered as above. Evaporation of the ethyl acetate gave a solid (19.8 g, 98%).

References:

Dhanak, Dashyant;Knight, Steven David US2003/100580, 2003, A1

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