6-Methoxy-8-quinolinamine → HCID 615723, compound

HRID 2379623Notes

Reaction equation

HRID 2379623 reaction equation
COC1C=C2C(=C(N)C=1)[N:9]=CC=C2.C(OC(=O)C)(=O)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[C:31]([NH:33][C:34]([CH3:36])=[O:35])[CH:32]=1)[N:29]=[CH:28][CH:27]=[CH:26]2>N1C=CC=CC=1>[NH2:9][C:24]1[C:23]([O:22][CH3:21])=[CH:32][C:31]([NH:33][C:34]([CH3:36])=[O:35])=[C:30]2[C:25]=1[CH:26]=[CH:27][CH:28]=[N:29]2

Participants

5

Reactant 3

HCID 70236-Methoxy-8-quinolinamineHCID 7918Acetic AnhydrideHCID 258762n-(6-methoxyquinolin-8-yl)acetamide

Product 1

HCID 615723HCID 615723, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Commercially available 6-methoxy-8-aminoquinoline (Chemical Procurement Laboratories) was acetylated with acetic anhydride and pyridine. The resultant 6-methoxy-8-acetaminoquinoline was nitrated and reduced using the procedure described in Example 33 to give 5-amino-6-methoxy-8-acetaminoquinoline. This product was coupled with 2-(hexylthio)decanoic acid according to Example 25 and hydrolyzed with aqueous hydrochloric acid and isopropanol to give the title compound. Mass spectrum m/e: 459.3 (M+).

Sources & evidence

ORD record
ord-ac18cfb1d6ec4e5583af84d75fb41d89
Source dataset
uspto-grants-1994_11
Patent number
US05362878

Reaction notes

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