N-(3-chloro-4-fluorophenyl)acetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Acetic anhydride (30 mL) was added at room temperature dropwise to 3-chloro-4-fluoroaniline (13.0 g, 0.1 mol) and stirred for 3 h. The reaction mixture was poured on ice (300 g) and the solid was filtered and dried to afford N-(3-chloro-4-fluorophenyl)acetamide (18.4 g, 98%) as a white solid. mp 96-97° C.; IR (KBr) 3303, 1671 cm-1 ; 1H NMR (CDCl3) δ 2.20 (s, 3H, CH3), 7.05 (t, J=8.9 Hz, 1H), 7.28 (m,1H), 7.66 (d, J=4.6 Hz, 1H), 8.05 (s, 1H, NH); Mass (m/z) 187 (M+). The reaction mixture was poured on ice (300 g) the solid was filtered dried

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A suspension of lithium aluminium hydride (44.1 g, 1.16 mmol) in absolute ether (700 ml) is treated dropwise with a solution of 3'-chloro-4'-fluoroacetanilide (BE Patent No. 891537; 109 g, 0.576 mol) in absolute THF (350 ml). The suspension obtained is stirred for 2 hours, then cooled to 0° and treated with a Rochelle salt solution (350 ml). The crystals obtained are filtered off and washed with ether. The organic solution is dried over magnesium sulphate and the solvent is distilled off under reduced pressure. There are obtained 97.5 g (97.5%) of 3-chloro-N-ethyl-4-fluoroaniline as an amorphous material. The suspension obtained cooled to 0° The crystals obtained are filtered off washed with ether The organic solution is dried over magnesium sulphate the solvent is distilled off under reduced pressure

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

Procedure: To a solution of N-(3-chloro-4-fluorophenyl)acetamide (55 g) in concentrated sulfuric acid (165 ml) was added dropwise concentrated nitric acid (d 1.42, 154 ml) at 5°-10° C. during an hour with stirring in an ice-salt bath. After stirring for an hour at the same temperature, the reaction mixture was poured into ice water. The resulting precipitate was collected by filtration, sufficiently washed with water and recrystallized from acetonitrile to give the title compound (48.9 g) as yellow needles, mp 114°-115° C. After stirring for an hour at the same temperature The resulting precipitate was collected by filtration sufficiently washed with water recrystallized from acetonitrile

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

Procedure: To 3-chloro-4-fluoroaniline (100 g) was slowly added acetic anhydride (200 ml). After allowed to stand for 30 minutes, the reaction mixture was poured into water (1 litter). The resulting precipitate was collected by filtration and recrystallized from aqueous ethanol to give the title compound (119.4 g), mp 118°-119° C. The resulting precipitate was collected by filtration recrystallized from aqueous ethanol

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

Procedure: Acetic anhydride (30 mL) was added at room temperature dropwise to 3-chloro-4-fluoroaniline (13.0 g, 0.1 mol) and stirred for 3 h. The reaction mixture was poured on ice (300 g) and the solid was filtered and dried to afford N-(3-chloro-4-fluorophenyl)acetamide (18.4 g, 98%) as a white solid. mp 96-97° C.; IR (KBr) 3303, 1671 cm-1 ; 1H NMR (CDCl3) δ 2.20 (s, 3H, CH3), 7.05 (t, J=8.9 Hz, 1H), 7.28 (m,1H), 7.66 (d, J=4.6 Hz, 1H), 8.05 (s, 1H, NH); Mass (m/z) 187 (M+). The reaction mixture was poured on ice (300 g) the solid was filtered dried