Hydrochloric Acid → HCID 12802771, compound

Iron powder (18 g.) was added over 40 minutes to a stirred solution of 1-(4-chlorobenzyl)-1,2-dihydro-6-nitro-2-oxoquinol-4-ylacetic acid (13 g.) in 50% v/v aqueous acetic acid (200 ml.) at 90° C. When the addition was completed, the mixture was stirred a further 70 minutes at 90° C. and then poured into an ice-water mixture (700 ml.). The mixture was adjusted to pH 1 with hydrochloric acid, and then filtered. The filtrate was adjusted to pH 6 with ammonium hydroxide solution, and the resulting mixture filtered. The solid residue (13 g.) was dissolved as far as possible in 2 N-sodium hydroxide solution, and the mixture was filtered. The filtrate was adjusted to pH 6 with glacial acetic acid, and the precipitated solid was filtered off, stirred with hot water (85° C., 200 ml.) and filtered while hot to give 6-amino-1-(4-chlorobenzyl)-1,2-dihydro-2-oxoquinol-4-ylacetic acid, m.p. 196°-9° C., (decomposition) in 52% yield.

1. additionWhen the addition
2. filtrationfiltered
3. filtrationthe resulting mixture filtered
4. dissolutionThe solid residue (13 g.) was dissolved as far as possible in 2 N-sodium hydroxide solution
5. filtrationthe mixture was filtered
6. filtrationthe precipitated solid was filtered off
7. stirringstirred with hot water (85° C., 200 ml.)
8. filtrationfiltered while hot

ORD record

ord-0a2d070d435847e3af65ca21944a2ba1

Source dataset

uspto-grants-1980_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04187310