Arsenic Acid → Isoquinoline

HRID 1681755Notes

Reaction equation

HRID 1681755 reaction equation
[C:1]1(N)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1N.[N+]([NH:12][C:13]1[CH:18]=CC=CC=1)([O-])=O.S(=O)(=O)(O)O.[As](=O)(O)(O)O.[N+]([C:32]1C=C(S(O)(=O)=O)C=CC=1)([O-])=O>OCC(CO)O>[CH:32]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:13][N:12]=1

Participants

7

Reactant 5

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

Product 1

HCID 8405Isoquinoline

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 isoquinoline 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 nitroquinoline, 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, glycerine and m-nitrobenzene sulfonic acid) to yield the phenanthroline.

Workup

  1. customIn a Skraup synthesis

Sources & evidence

ORD record
ord-1c2e38849e494a9b971e0eb819b52ee1
Source dataset
uspto-grants-1992_12
Patent number
US05173489

Reaction notes

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