6-amino-2,4-dichloro-3-methylphenol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Amino-2.4 dichloro-3-metylphenol (1.9 g, 10 mmol), 2-chloroacetyl chloride (1.2 g, 11 mmol) and K2CO3 (3.0 g, 22 mmol) were mixed according to GP1 to give the title compound as a crude (80MF2225) (2.33 g).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 500 ml 3-necked round bottom flask, equipped with a stir bar, addition funnel, and N2 inlet, was placed 10 g (52 mmoles) of 6-amino-2,4-dichloro-3-methylphenol and 150 ml of ethyl acetate. With stirring a solution resulted. To this solution was added 4.53 g (57.2 mmoles) of pyridine. This solution was stirred for 5 minutes during which time 10.95 g (54.6 mmoles) of 3,5-dimethoxybenzoyl chloride (Aldrich Chemical Co., CAS RN 17213-57-9) was dissolved in 75 ml of ethyl acetate and placed in an addition funnel. This solution was added dropwise to the reaction vessel over a 30 minute period. A precipitate formed almost immediately. After complete addition the reaction mixture was allowed to stir overnight. Thin layer chromatography (5/95 acetone/CH2Cl2) analysis of the reaction mixture indicated no starting material and primarily one new spot and a spot at the origin. The reaction mixture was poured into a separatory funnel and washed 2 times with a cold 10% hydrochloric acid solution followed by 2 times with a saturated sodium chloride solution and the organic layer was dried over sodium sulfate. The sodium sulfate was collected on a gravity filter and the filtrate was concentrated to a salmon colored solid. This solid was recrystallized from refluxing ethanol. The resulting crystals were collected on a medium sintered glass funnel, and dried by sucking air through for three hours. 8.9 g of desired product was obtained, a 48% purified yield. Into a 500 ml 3-necked round bottom flask, equipped with a stir bar, addition funnel, and N2 inlet resulted placed in an addition funnel This solution was added dropwise to the reaction vessel over a 30 minute period A precipitate formed almost immediately After complete addition the reaction mixture to stir overnight The reaction mixture was poured into a separatory funnel washed 2 times with a cold 10% hydrochloric acid solution the organic layer was dried over sodium sulfate The sodium sulfate was collected on a gravity filter the filtrate was concentrated to a salmon This solid was recrystallized from refluxing ethanol The resulting crystals were collected on a medium sintered glass funnel dried through for three hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Amino-2.4 dichloro-3-metylphenol (1.9 g, 10 mmol), 2-chloroacetyl chloride (1.2 g, 11 mmol) and K2CO3 (3.0 g, 22 mmol) were mixed according to GP1 to give the title compound as a crude (80MF2225) (2.33 g).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Amino-2.4 dichloro-3-metylphenol (1.9 g, 10 mmol), 2-chloroacetyl chloride (1.2 g, 11 mmol) and K2CO3 (3.0 g, 22 mmol) were mixed according to GP1 to give the title compound as a crude (80MF2225) (2.33 g).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Amino-2.4 dichloro-3-metylphenol (1.9 g, 10 mmol), 2-chloroacetyl chloride (1.2 g, 11 mmol) and K2CO3 (3.0 g, 22 mmol) were mixed according to GP1 to give the title compound as a crude (80MF2225) (2.33 g).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product from Example 9, Stage 1a (4.8 g), was stirred in acetic acid (20 ml) and acetic anhydride (5 ml) was added in one portion. Stirring was continued for 1hour after the initially exothermic reaction had subsided. The product was isolated by filtration and recrystallised from aqueous ethanol. after the initially exothermic reaction The product was isolated by filtration recrystallised from aqueous ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Amino-2.4 dichloro-3-methylphenol (1.9 g, 10 mmol), 2-chloroacetyl chloride (1.2 g, 11 mmol) and K2CO3 (3.0 g, 22 mmol) were mixed according to GP1 to give the title compound as a crude (80MF2225) (2.33 g).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Amino-2.4 dichloro-3-metylphenol (1.9 g, 10 mmol), 2-chloroacetyl chloride (1.2 g, 11 mmol) and K2CO3 (3.0 g, 22 mmol) were mixed according to GP1 to give the title compound as a crude (80MF2225) (2.33 g).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 500 ml 3-necked round bottom flask, equipped with a stir bar, addition funnel, and N2 inlet, was placed 10 g (52 mmoles) of 6-amino-2,4-dichloro-3-methylphenol and 150 ml of ethyl acetate. With stirring a solution resulted. To this solution was added 4.53 g (57.2 mmoles) of pyridine. This solution was stirred for 5 minutes during which time 10.95 g (54.6 mmoles) of 3,5-dimethoxybenzoyl chloride (Aldrich Chemical Co., CAS RN 17213-57-9) was dissolved in 75 ml of ethyl acetate and placed in an addition funnel. This solution was added dropwise to the reaction vessel over a 30 minute period. A precipitate formed almost immediately. After complete addition the reaction mixture was allowed to stir overnight. Thin layer chromatography (5/95 acetone/CH2Cl2) analysis of the reaction mixture indicated no starting material and primarily one new spot and a spot at the origin. The reaction mixture was poured into a separatory funnel and washed 2 times with a cold 10% hydrochloric acid solution followed by 2 times with a saturated sodium chloride solution and the organic layer was dried over sodium sulfate. The sodium sulfate was collected on a gravity filter and the filtrate was concentrated to a salmon colored solid. This solid was recrystallized from refluxing ethanol. The resulting crystals were collected on a medium sintered glass funnel, and dried by sucking air through for three hours. 8.9 g of desired product was obtained, a 48% purified yield. Into a 500 ml 3-necked round bottom flask, equipped with a stir bar, addition funnel, and N2 inlet resulted placed in an addition funnel This solution was added dropwise to the reaction vessel over a 30 minute period A precipitate formed almost immediately After complete addition the reaction mixture to stir overnight The reaction mixture was poured into a separatory funnel washed 2 times with a cold 10% hydrochloric acid solution the organic layer was dried over sodium sulfate The sodium sulfate was collected on a gravity filter the filtrate was concentrated to a salmon This solid was recrystallized from refluxing ethanol The resulting crystals were collected on a medium sintered glass funnel dried through for three hours