Acetic Acid → HCID 18435892, compound

HRID 351282Notes

Reaction equation

HRID 351282 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.[N+]([O-])([O-])=O.[K+].[N+:17]([O-])(O)=O.[C:21]([OH:24])(=O)[CH3:22]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:17][C:21](=[O:24])[CH3:22])=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 24434Potassium NitrateHCID 30173648-Methylisoquinoline

Product 1

HCID 18435892HCID 18435892, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

In Scheme 12, the 8-methylisoquinoline (obtained as described above) is nitrated with a suitable nitrating agent such as potassium nitrate in sulfuric acid or a mixture of nitric acid, sulfuric acid and acetic acid to yield 5-nitro-8-methylsioquinoline, which is reduced and then acetylated to give the N-(8-methyl-isoquinolin-5-yl)-acetamide. This amide may be brominated by a radical brominating agent such as N-bromosuccinimide/benzoyl peroxide to give the dibromo isoquinoline acetamide. The dibromo intermediate may then be hydrolyzed in the presence of base to yield the deprotected aldehyde aminoisoquinoline, which may be further elaborated by the chemistry illustrated in Schemes 5 and 6 to the target ureas.

Workup

  1. customto yield 5-nitro-8-methylsioquinoline, which

Sources & evidence

ORD record
ord-710ce2747b6348859277892b350d92a6
Source dataset
uspto-grants-2007_02
Patent number
US07183411B2

Reaction notes

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