Hydrochloric Acid → HCID 12802771, compound

HRID 1448825Notes

Reaction equation

HRID 1448825 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=3)[C:10]([CH2:20][C:21]([OH:23])=[O:22])=[CH:9][C:8]2=[O:24])=[CH:4][CH:3]=1.Cl>[Fe].C(O)(=O)C>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:7]([CH2:6][C:5]1[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:8](=[O:24])[CH:9]=[C:10]2[CH2:20][C:21]([OH:23])=[O:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12802770HCID 12802770, compound

Product 1

HCID 12802771HCID 12802771, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0a2d070d435847e3af65ca21944a2ba1
Source dataset
uspto-grants-1980_02
Patent number
US04187310

Reaction notes

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