4-Chloroaniline → HCID 23037169, compound
Reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1)([O-:11])=[O:10]>>[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([N:6]([C:15]2[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)[C:5]2[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10]Participants
Procedure
Bis(p-nitrophenyl)-p-chlorophenylamine (3.70 grams, 0.010 mol) obtained by the Ullmann condensation of p-chloroaniline and p-nitroiodobenzene was mixed with 125 ml of N,N-dimethylformamide and 2,50 grams (0.045 mol) of iron powder, and dilute hydrochloric acid prepared using 1.5 ml of concentrated hydrochloric acid and 4 ml of water was added to the mixture which was then reacted for 1 hour at 100° C. The mixture was then neutralized by the addition of a saturated aqueous solution of sodium carbonate and the resulting mixture was filtered while hot. The filtrate was poured into 1.5 liters of ice water and 2.33 grams (yield 69%) of p-aminophenyl-p-nitrophenyl-p-chlorophenylamine was obtained on recovering the material which precipitated out by filtration.
Sources & evidence
- ORD record
- ord-9dbcf1c9fb8c4f48aaed6b438604d823
- Source dataset
- uspto-grants-1990_08
- Patent number
- US04948688
Reaction notes
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