Ammonia → 6-Nitro-8-quinolinecarboxylic acid

HRID 1756499Notes

Reaction equation

HRID 1756499 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[As](=O)(O)(O)O.S(=O)(=O)(O)O.N.O[CH2:26][CH:27]([CH2:29]O)O>C(O)(=O)C.O>[C:4]([C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[C:10]2[C:2]=1[N:1]=[CH:29][CH:27]=[CH:26]2)([OH:6])=[O:5]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 234Arsenic AcidHCID 753GlycerolHCID 1118Sulfuric AcidHCID 120322-Amino-5-nitrobenzoic acid

Product 1

HCID 1501526-Nitro-8-quinolinecarboxylic acidYield 83.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-amino-5-nitrobenzoic acid (4 g, 22 mM), glycerol (8 g), arsenic acid (80% in water) (20 g), and sulphuric acid (65%) (36 ml) was heated at reflux for 3.5 hours. After addition of water (100 ml), the pH was adjusted to 8 with concentrated ammonia and then to 3.5 with acetic acid. The resulting precipitate was filtered and dried to give 8-carboxy-6-nitroquinoline (4 g; 83%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-13e56a399767407285f32897d5013d70
Source dataset
uspto-grants-1995_08
Patent number
US05441949

Reaction notes

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