Ammonia → 8-Bromoquinoline-5-carbonitrile

0.60 g of concentrated hydrochloric acid was added dropwise to a mixture of 0.70 g of 5-amino-8-bromoquinoline and 3.15 ml of acetic acid, and the mixture was stirred for 1 hour at room temperature. At 0-50° C., 0.22 g of sodium nitrite in 0.45 ml of water were then added, and the mixture was stirred for 1 hour. After the addition of 20 mg of urea in 0.16 ml of water, stirring was continued at 0-50° C. for a further hour. This solution is added to a two-phase system of toluene/copper(I) cyanide solution which was prepared as follows: a solution of 0.79 g of copper(II) sulfate in 2.2 ml of water was added dropwise to a solution of 1.06 g of 10% strength ammonia solution and 0.77 g of sodium cyanide, and 6 ml of toluene were added to this mixture to form a lower layer. After stirring for 1 hour at room temperature, insoluble particles were filtered off and the solution was extracted with ethyl acetate. The organic phase was dried and the solvent was removed under reduced pressure.

1. stirringthe mixture was stirred for 1 hour
2. stirringstirring
3. waitwas continued at 0-50° C. for a further hour
4. customwas prepared
5. additionwere added to this mixture
6. customto form a lower layer
7. stirringAfter stirring for 1 hour at room temperature
8. filtrationinsoluble particles were filtered off
9. extractionthe solution was extracted with ethyl acetate
10. customThe organic phase was dried
11. customthe solvent was removed under reduced pressure

ORD record

ord-3db926f72e2f4320ac2c9690aeba2310

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06262074B1