N-(4-amino-2-chlorophenyl)pentanamide

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

Procedure: 2'-Chloro-4'-nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for one-half hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7.5 g., m.p. 96.5°-99° C. to maintain gentle boiling The resulting reaction mixture is refluxed for one-half hour filtered The filtrate is evaporated under reduced pressure the residue is triturated with water The solid that forms is collected (11.5 g.) recrystallized from cyclohexane to yield 7.5 g

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

Procedure: 2'-Chloro-4'-nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for 1/2 hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7,5 g., m.p. 96.5°-99° C. to maintain gentle boiling The resulting reaction mixture is refluxed for 1/2 hour filtered The filtrate is evaporated under reduced pressure the residue is triturated with water The solid that forms is collected (11.5 g.) recrystallized from cyclohexane to yield 7,5 g

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

Procedure: 2'-Chloro-4'nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for one-half hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7.5 g., m.p. 96.5°-99° C. to maintain gentle boiling The resulting reaction mixture is refluxed for one-half hour filtered The filtrate is evaporated under reduced pressure the residue is triturated with water The solid that forms is collected (11.5 g.) recrystallized from cyclohexane to yield 7.5 g

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

Procedure: 2'-Chloro-4'nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for one-half hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7.5 g., m.p. 96.5°-99° C. to maintain gentle boiling The resulting reaction mixture is refluxed for one-half hour filtered The filtrate is evaporated under reduced pressure the residue is triturated with water The solid that forms is collected (11.5 g.) recrystallized from cyclohexane to yield 7.5 g

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

Procedure: 2'-Chloro-4'-nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for one-half hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7.5 g., m.p. 96.5°-99° C. to maintain gentle boiling The resulting reaction mixture is refluxed for one-half hour filtered The filtrate is evaporated under reduced pressure the residue is triturated with water The solid that forms is collected (11.5 g.) recrystallized from cyclohexane to yield 7.5 g

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

Procedure: 2'-Chloro-4'-nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for one-half hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7.5 g., m.p. 96.5°-99° C. to maintain gentle boiling The resulting reaction mixture is refluxed for one-half hour filtered The filtrate is evaporated under reduced pressure the residue is triturated with water The solid that forms is collected (11.5 g.) recrystallized from cyclohexane to yield 7.5 g

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

Procedure: A mixture of 4'-amino-2'-chlorovaleranilide (2.27 g., 0.01 mole) anti-tricyclo[4.2.2.02,5 ]dec-3,9-diene-endo7,endo-8-dicarboxylic anhydride (2.02 g., 0.01 mole) and pyridine (20 ml.) is heated under reflux for twenty-four hours. The solvent is removed in vacuo and the residue (4.35 g., m.p. 120°-136° C.) is recrystallized from butyl chloride to give N-(3-chloro-4-valeramidophenyl)-antitricyclo[4.2.2.02,5 ]dec-3,9-diene-endo-7,endo-8-dicarboximide, m.p. 157.5°-159° C. is heated under reflux for twenty-four hours The solvent is removed in vacuo the residue (4.35 g., m.p. 120°-136° C.) is recrystallized from butyl chloride

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

Procedure: 2'-Chloro-4'-nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for one-half hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7.5 g., m.p. 96.5°-99° C. to maintain gentle boiling The resulting reaction mixture is refluxed for one-half hour filtered The filtrate is evaporated under reduced pressure the residue is triturated with water The solid that forms is collected (11.5 g.) recrystallized from cyclohexane to yield 7.5 g

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

Procedure: 2'-Chloro-4'-nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for 1/2 hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7,5 g., m.p. 96.5°-99° C. to maintain gentle boiling The resulting reaction mixture is refluxed for 1/2 hour filtered The filtrate is evaporated under reduced pressure the residue is triturated with water The solid that forms is collected (11.5 g.) recrystallized from cyclohexane to yield 7,5 g

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

Procedure: 2'-Chloro-4'nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for one-half hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7.5 g., m.p. 96.5°-99° C. to maintain gentle boiling The resulting reaction mixture is refluxed for one-half hour filtered The filtrate is evaporated under reduced pressure the residue is triturated with water The solid that forms is collected (11.5 g.) recrystallized from cyclohexane to yield 7.5 g