Water → (2-Amino-3-chlorophenyl)methanol

A solution of 28.9 g (155 mmol) of methyl 3-chloroanthranilate in 100 ml of ether was added dropwise to a stirred suspension of 7.67 g (202 mmol) of lithium aluminum hydride in 400 ml of ether. After stirring for five hours at room temperature, the grey mixture was treated sequentially with 7.7 ml of water, 7.7 ml of 15% sodium hydroxide and 23 ml of water. The reaction mixture was filtered, and the filtrate was evaporated at reduced pressure. The oily residue was dissolved in ether, and precipitation of the product was induced by addition of hexane. The product was collected by filtration to yield a tan solid in 67% yield, mp 56°-68° C. IR and 1H NMR spectra were in agreement with the assigned structure.

1. filtrationThe reaction mixture was filtered
2. customthe filtrate was evaporated at reduced pressure
3. dissolutionThe oily residue was dissolved in ether
4. customprecipitation of the product
5. additionwas induced by addition of hexane
6. filtrationThe product was collected by filtration
7. customto yield a tan solid in 67% yield, mp 56°-68° C

ORD record

ord-91da085633ca4255a9408ca93746e108

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04818273