Arsenic Acid → Isoquinoline

HRID 1463653Notes

Reaction equation

HRID 1463653 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-quinoline 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-nitrobenzenesulfonic acid) to yield the phenanthroline.

Workup

  1. customIn a Skraup synthesis

Sources & evidence

ORD record
ord-9c6fd67df48547c3b04d9c5f1f071b78
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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