Arsenic Acid → 2-Aminoquinoline

HRID 1648127Notes

Reaction equation

HRID 1648127 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1N.[N+]([NH:12][C:13]1C=CC=[CH:15][CH:14]=1)([O-])=O.S(=O)(=O)(O)O.[As](=O)(O)(O)O.[N+](C1C=C(S(O)(=O)=O)C=CC=1)([O-])=O>OCC(CO)O>[NH2:12][C:13]1[CH:14]=[CH:15][C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:8]=1

Participants

7

Reactant 5

HCID 234Arsenic AcidHCID 1118Sulfuric AcidHCID 7243O-PhenylenediamineHCID 73873-Nitrobenzenesulfonic acidHCID 61191N-Nitroaniline

Product 1

HCID 113792-Aminoquinoline

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

In a Skraup synthesis, a phenylene diamine (148) or a nitroaniline is reacted with glycerine (149) and sulfuric acid or arsenic acid and an oxidizing agent, such as m-nitrobenzene sulfonic acid (Scheme 66). ##STR86## An intermediate amino- or nitro-guinoline or isoguinoline is produced. In the case of the amino-quinoline, it is not isolated, as it reacts immediately with excess reagents to yield the phenanthroline. If a nitro-aniline has been used to produce a nitroguinoline, it is isolated and purified if necessary. This often removes large amounts of tars produced by the Skraup synthesis. The nitro group is then reduced by standard conditions to yield an aminoquinoline. The aminoquinoline is then subjected to another Skraup reaction (sulfuric or arsenic acid, or both, glycerins and m-nitrobenzenesulfonic acid) to yield the phenanthroline.

Workup

  1. customIn a Skraup synthesis
  2. custom##STR86## An intermediate amino- or nitro-guinoline or isoguinoline is produced

Sources & evidence

ORD record
ord-5267d3c63ee54a1aa34f2751ed98006e
Source dataset
uspto-grants-1995_07
Patent number
US05434264

Reaction notes

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