4-Methoxy-3-nitrobenzenamine

orange red solid

A suspension of S-10 (4 g, 21.5 mMol) in 40 mL dichloromethane was slowly added to cold 95percent sulfuric acid (21 g, 215 mMol) while maintaining the batch temperature at 0+/-5° C. After the addition the mixture was agitated at 0+/-5° C. for approximately 3 h. The agitation was stopped and the bottom acid layer was slowly transferred to 40 mL of water while maintaining the temperature at <20° C. To the diluted reaction mixture was slowly added ammonium hydroxide solution at <20° C. until pH was 6-11. The mixture was extracted twice with dichloromethane. The combined organic solution was washed with brine, dried over MgSOWeigh 63g 95percent concentrated sulfuric acid in 500mL three bottles, Cool to 0 ° C.12 g of compound 12, Suspended in 120 mL of dichloromethane, Formulated as a suspension, The suspension was added dropwise to the cold concentrated sulfuric acid, During the dropping process, the control temperature is about 0 ° C, After completion of the drop to maintain this temperature reaction for about 3h, The reaction solution was separated, Take the layer of acid, 120mL water to about 0 , The acid layer slowly added to cold water, The process to keep the temperature does not exceed 20 , After completion of the dropwise addition, ammonia water was added to the diluted reaction solution until the pH was 6-11, Dripping process temperature does not exceed 20 , Extracted with 120 mL x 2 DCM, The organic phase was washed with saturated brine and concentrated.To give 8.7 g of a dark brown viscous oil, Yield 80.3percent.The prepared 2, 4-dinitroanisole (II) was dissolved in 2 kg of methanol solution, followed by the addition of 60 g of Example 1PdCu / graphene bimetallic catalyst prepared by catalytic hydrogenation reduction reaction, Reaction pressure is 1Mpa, Reaction temperature is 60 , Reaction time 35min, The reaction is over.After the filter to remove the catalyst, Distillation recovery of methanol, Washed, 749.26 g of 4-amino-2-nitroanisole (III) (HPLC purity 99.6percent) was obtained, Yield 98.1percent.REFERENCE EXAMPLE 57 4-Methoxy-3-nitroaniline 4-Methoxy-3-nitroaniline (4) 2-Nitro-4-amino-1-chlorobenzene 8 (6.2 g, 2.43 mol)Add inorganic alkali hydroxide solution and catalyst potassium iodide, Reaction occurs at 55°C, 2-Nitro-4-amino-1-phenol 9 (7.32 g, 3.98 mol) was generated, In 2-nitro-4-amino-1-phenol 9 (7.32 g, 3.98 mol)Add chloromethane (460ml) to1-methoxy-2-nitro-4-phenylamine 10 (9.34 g, 4.21 mol) was formed;Acryloyl chloride 11 is added to 1-methoxy-2-nitro-4-phenylamine 10, Substitution reaction occurs, 1-methoxy-2-nitro-4-acrylamidobenzene 12 (7.32 g, 4.32 mol) was formed.

Molecular Weight:168.15
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:168.05349212
Monoisotopic Mass:168.05349212
Topological Polar Surface Area:81.1
Heavy Atom Count:12
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes