Allyl chloride → N-allyl-2-methyl-4-nitroaniline
Reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH3:13])=O.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Cl)[CH:21]=C.[OH-].[Na+]>CN(C)C=O>[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH3:13])[CH:20]=[CH2:21]Participants
Conditions
- Temperature
- 70 °C
Procedure
60 g (0.33 mol) of N-formyl-2-methyl-4-nitroaniline were dissolved in 500 ml of dimethylformamide. 184 g (1.33 mol) of potassium carbonate were added, and the resultant solution was warmed to 50° C. 152.8 g (2 mol) of allyl chloride were added dropwise in the course of 50 minutes to the mixture at 50° C. When the alkylation reaction was complete, the resultant reaction mixture was warmed to 70° C. and 350 g of 1 N sodium hydroxide solution were slowly added dropwise. The resultant mixture was stirred at 70° C. for 2.5 hours and subsequently poured into 3 l of ice water. The precipitate was filtered off with suction, washed with water until neutral and subsequently dried at 50° C. under reduced pressure, to give 61 g of N-allyl-2-methyl-4-nitroaniline (yield: 95%), which was recrystallized as described under section 1.4 and then had the same physical chemical properties as the compound prepared in accordance with section 1.4.
Workup
- customWhen the alkylation reaction
- customthe resultant reaction mixture
- filtrationThe precipitate was filtered off with suction
- washwashed with water until neutral and
- customsubsequently dried at 50° C. under reduced pressure
Sources & evidence
- ORD record
- ord-6793681620f340fcad052b9ad06e6bc9
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05103060
Reaction notes
Loading…