2-amino-4,5-dichlorobenzaldehyde

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

Procedure: 3,4-Dichloro-6-aminobenzaldehyde (2.85 g, 15 mmol) was stirred with dimethylmalonate (10 ml) at 140° C. for 20 h. The mixture was diluted with ethyl ether (100 ml). The precipitate was collected, washed twice with ethyl ether and dried in vacuo to give 2.86 g of methyl 6,7-dichloro-2-hydroxyquinoline-3-carboxylate. The precipitate was collected washed twice with ethyl ether dried in vacuo

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

Procedure: 3,4-Dichloro-6-nitrobenzaldehyde (4.40 g, 20 mmol) was dissolved in 50% aqueous ethanol (200 ml) at 50°-60° C. and the solution was added to a solution of iron(II) sulfate heptahydrate (27.8 g, 100 mmol) in water (200 ml) at 90° C. Concentrated (25%) aqueous ammonia (50 ml) was added in several portions with intensive stirring while the temperature was kept close to the boiling point. The mixture was refluxed for 5-10 min. and cooled. The precipitate was filtered off and washed with ethanol. The filtrate was concentrated in vacuo until most of the ethanol was removed. The resulting precipitate was collected, washed with water and dried in vacuo at 40°-50° C. to give 3.3 g of 3,4-dichloro-6-aminobenzaldehyde. Concentrated (25%) aqueous ammonia (50 ml) was added in several portions was kept close to the boiling point The mixture was refluxed for 5-10 min. cooled The precipitate was filtered off washed with ethanol The filtrate was concentrated in vacuo until most of the ethanol was removed The resulting precipitate was collected washed with water dried in vacuo at 40°-50° C.

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

Procedure: 3,4-Dichloro-6-aminobenzaldehyde (2.85 g, 15 mmol) was stirred with dimethylmalonate (10 ml) at 140° C. for 20 h. The mixture was diluted with ethyl ether (100 ml). The precipitate was collected, washed twice with ethyl ether and dried in vacuo to give 2.86 g of methyl 6,7-dichloro-2-hydroxyquinoline-3-carboxylate. The precipitate was collected washed twice with ethyl ether dried in vacuo

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

Procedure: 3,4-Dichloro-6-nitrobenzaldehyde (4.40 g, 20 mmol) was dissolved in 50% aqueous ethanol (200 ml) at 50°-60° C. and the solution was added to a solution of iron(II) sulfate heptahydrate (27.8 g, 100 mmol) in water (200 ml) at 90° C. Concentrated (25%) aqueous ammonia (50 ml) was added in several portions with intensive stirring while the temperature was kept close to the boiling point. The mixture was refluxed for 5-10 min. and cooled. The precipitate was filtered off and washed with ethanol. The filtrate was concentrated in vacuo until most of the ethanol was removed. The resulting precipitate was collected, washed with water and dried in vacuo at 40°-50° C. to give 3.3 g of 3,4-dichloro-6-aminobenzaldehyde. Concentrated (25%) aqueous ammonia (50 ml) was added in several portions was kept close to the boiling point The mixture was refluxed for 5-10 min. cooled The precipitate was filtered off washed with ethanol The filtrate was concentrated in vacuo until most of the ethanol was removed The resulting precipitate was collected washed with water dried in vacuo at 40°-50° C.