Sodium Hydroxide → (2-Amino-3-chlorophenyl)amine

12.5 g (72.4 mmol) of 3-chloro-2-nitroaniline was dissolved in methanol (250 ml), and a solution prepared by dissolving 57.2 g (253 mmol) of tin (II) chloride dihydrate in concentrated hydrochloric acid (75 mL) was added dropwise. The reaction mixture was heated with stirring for 3 hours, and concentrated under reduced pressure. Water was added to the residue thus obtained, and the solution was alkalinized with a 25% aqueous solution of sodium hydroxide, and extracted with methylene chloride. The extracted organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, to obtain 10.5 g (yield: >99%) of 3-chloro-1,2-phenylenediamine as a pale magenta-colored liquid.

1. customa solution prepared
2. additionwas added dropwise
3. temperatureThe reaction mixture was heated
4. concentrationconcentrated under reduced pressure
5. additionWater was added to the residue
6. customthus obtained
7. extractionextracted with methylene chloride
8. dry with materialThe extracted organic layer was dried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-b204f31e85c340d3b88e162962a1525c

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389523B2