Hydrochloric Acid → HCID 12802771, compound

HRID 1390288Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:28]=[CH:27][C:7]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=3)[C:12]([CH2:22][C:23]([OH:25])=[O:24])=[CH:11][C:10]2=[O:26])=[CH:6][CH:5]=1.Cl>C(O)(=O)C>[NH2:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:9]([CH2:8][C:7]1[CH:27]=[CH:28][C:4]([Cl:3])=[CH:5][CH:6]=1)[C:10](=[O:26])[CH:11]=[C:12]2[CH2:22][C:23]([OH:25])=[O:24]

Participants

Conditions

Temperature: 90 °C

Procedure

Iron powder (18g.) was added over 40 minutes to a stirred solution of 1-(4-chlorobenzyl)-1,2-dihydro-6-nitro-2-oxoquinol-4-ylacetic acid (13g.) 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 (13g.) was dissolved as far as possible in 2N-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.

Workup

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

Sources & evidence

ORD record: ord-707ac3ee247544379a58205642281795
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04138490

Reaction notes

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