Benzyl Chloride → Benzenamine, 5-chloro-4-nitro-2-(phenylmethoxy)-

HRID 1018721Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CC(C)=O>[CH2:21]([O:12][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[C:6]([Cl:8])=[CH:7][C:2]=1[NH2:1])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 55 °C

Procedure

In a 500-ml flask, place 18.9 g (0.1 m) of 2-amino-4-chloro-5-nitrophenol (1) and 120 ml of acetone, and heat to 50° C. Add 7.2 g (0.1 m×1.15@90%) of KOH flakes and stir at 55° C. to make a deep red brown solution. Add 6.9 g (0.05 m) of potassium carbonate, 0.8 g of tetrabutyl ammonium bromide and 14.6 g (0.1 m×1.15) of benzyl chloride. Stir the reaction mixture under reflux with fast stirring for 3 hrs. Cool the mixture to room temperature and add 240 ml of water slowly. Stir the resulting slurry and cool to 20° C. Collect solid, wash with water and heptane, and dry in an air oven to give 25.4 g (91%) of 2-benzyloxy-5-chloro-4-nitroaniline (2) as yellow granular solids.

Workup

stirringStir the reaction mixture
temperatureunder reflux
stirringwith fast stirring for 3 hrs
temperatureCool the mixture to room temperature
stirringStir the resulting slurry
temperaturecool to 20° C
customCollect solid
washwash with water and heptane
customdry in an air oven

Sources & evidence

ORD record: ord-bd1da8af801342f28dbeb56a719d7c07
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06482953B1

Reaction notes

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