Potassium Nitrate → HCID 12802770, compound

HRID 1390287Notes

Reaction equation

HRID 1390287 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][C:18]([OH:20])=[O:19])=[CH:9][C:8]2=[O:21])=[CH:4][CH:3]=1.[N+:24]([O-])([O-:26])=[O:25].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][C:13]([N+:24]([O-:26])=[O:25])=[CH:14][CH:15]=3)[C:10]([CH2:17][C:18]([OH:20])=[O:19])=[CH:9][C:8]2=[O:21])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 12802705HCID 12802705, compound

Product 1

HCID 12802770HCID 12802770, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Chlorobenzyl)-1,2-dihydro-2-oxoquinol-4-ylacetic acid (33 g.) was added to concentrated sulphuric acid (210 ml.) at 0° C. The mixture was stirred at 0° C. and potassium nitrate(11g.) was added in small portions over 8 minutes. The mixture was then stirred at 0° C. for a further 10 minutes and then for 2 hours at room temperature. The mixture was poured into an ice-water mixture (2.5 l.), and the precipitated solid was filtered off. The dried solid was crystallised from 3/1 v/v dimethylformamide-ethanol to give 1-(4-chlorobenzyl)-1,2-dihydro-6-nitro-2-oxoquinol-4-ylacetic acid, m.p. 217-9° C., in 85% yield.

Workup

  1. stirringThe mixture was then stirred at 0° C. for a further 10 minutes
  2. filtrationthe precipitated solid was filtered off
  3. customThe dried solid was crystallised from 3/1 v/v dimethylformamide-ethanol

Sources & evidence

ORD record
ord-f0cfb774ae854cc3bd438af9a18deba5
Source dataset
uspto-grants-1979_02
Patent number
US04138490

Reaction notes

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