Nitric Acid → HCID 178526772, compound

HRID 1672307Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 944Nitric Acid

HCID 178516426HCID 178516426, compound

Product 1

HCID 178526772HCID 178526772, compound

Conditions

Temperature: 87.5 °C

Procedure

20 g (0.111 mol) 7-chloro-quinolin-4-ol (Aldrich) are added during 5 min to 200 ml nitric acid (66%) heated at 85-90° C. After 4.5 h the title compound starts to precipitate as a crystalline solid. The reaction mixture is stirred for a total of 5.5 h. The hot mixture is filtered off, and the residue washed first with conc. nitric acid, then with boiling water followed by acetone. Additional material can be isolated from the mother liquors. The solid materials are combined and heated in boiling methanol for 3 h to dissolve some un-reacted starting material. The insoluble title compound is filtered off and dried for 16 h at 70° C. (high vacuum). mp: >300° C., MS: 225 (M++1); HPLC: tret=7.30 min (Grad 1).

Sources & evidence

ORD record: ord-6e710b6e88ea495e8f469f895da3a961
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998972B2

Reaction notes

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