Sodium hydride → 2-Methoxyquinolin-8-amine

HRID 2290652Notes

Reaction equation

HRID 2290652 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[CH:8]=[CH:7]2.[CH3:13][O-:14].[Na+].[H-].[Na+].[H][H]>CN(C=O)C.CO>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:14][CH3:13])[CH:8]=[CH:7]2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3465192-Chloroquinolin-8-amineHCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 4368672-Methoxyquinolin-8-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

Thus, the 8-amino-2-chloroquinoline VI was allowed to react with a solution of sodium methylate in DMF (prepared under nitrogen by adding sodium hydride to a solution of methanol in DMF accompanied by the liberation of hydrogen). This procedure afforded 8-amino-2-methoxyquinoline VII. The introduction of the 8-(4-amino-1-methylbutyl) side chain was accomplished in the same manner as for the COMPARATIVE COMPOUND (U.S. Pat. No. 4,431,801). Thus intermediate VII was treated with 4-iodo-1-phthalimidopentane to give the target precursor 8-(4-phthalimido-1-methylbutylamino)quinoline VIII. The phthalimido group was removed with hydrazine to give the title compound free base IX. The free base was treated with succinic acid in a suitable solvent system to give the 2-methoxy target compound X as the succinic acid salt.

Workup

  1. customprepared under nitrogen

Sources & evidence

ORD record
ord-e85f0bb320e04f9ba5e71a90b5ed8640
Source dataset
uspto-grants-1986_10
Patent number
US04617394

Reaction notes

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