Water → 6-Nitroquinoline-2-carboxylic acid

HRID 1756505Notes

Reaction equation

HRID 1756505 reaction equation
[CH:1](=[C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=2)[NH:9]1)C1C=CC=CC=1.[O-:21][Mn](=O)(=O)=O.[K+].[OH2:27]>N1C=CC=CC=1>[C:1]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=2)[N:9]=1)([OH:21])=[O:27]

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 67619679HCID 67619679, compound

Product 1

HCID 123242586-Nitroquinoline-2-carboxylic acidYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-benzylidene-6-nitroquinoline (4.9 g; 17.7 mM) in pyridine (36.6 ml) and water (8 ml) was added portion wise KMnO4 (7.5 g; 47.8 mM) keeping the temperature between 18 and 20° C. After filtration on celite, the solution was acidified (pH3), at 0° C., with H2SO4 (65%). The resulting precipitate was filtered, washed with water and ether and then dried to give 2-carboxy-6-nitroquinoline (1.5 g; 39%).

Workup

  1. customthe temperature between 18 and 20° C
  2. filtrationAfter filtration on celite
  3. customat 0° C.
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water and ether
  6. customdried

Sources & evidence

ORD record
ord-7aa3c28a5ebf48368cae92f6cd761c7f
Source dataset
uspto-grants-1995_08
Patent number
US05441949

Reaction notes

Loading…