HCID 20183595, compound → HCID 20183608, compound

HRID 255560Notes

Reaction equation

HRID 255560 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][C:13]=2[N+:22]([O-])=O)=[CH:5][CH:4]=1.[H][H]>C1(C)C=CC=CC=1.[Pt]>[NH2:22][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:12]=1[NH:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

5

Reactant 2

HCID 20183595HCID 20183595, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20183608HCID 20183608, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

Using the method of Example 26, 20.4 g (0.063 mole) of 4-[2-(4-methoxyphenyl)ethylamino]-3-nitroquinoline was reduced by hydrogen in 300 ml of toluene with 5% platinum on charcoal. The solvent was then evaporated to provide a residue of 3-amino-4-[2-(4-methoxyphenyl)ethylamino]quinoline. To this residue was added 28 g (0.19 mole) of triethyl orthoformate and the mixture was heated at about 125° C. for two hours. To this mixture was added about 100 ml of aqueous hydrochloric acid and the mixture was heated on a steam bath for thirty minutes. After cooling, the precipitate was separated by filtration, washed sequentially with isopropanol and diethyl ether, and dried. To the solid was added water and ammonium hydroxide, after which the mixture was cooled and the solid was separated by filtration. A portion (3.5 g) of the solid was dissolved in isopropanol, and acidified with hydrochloric acid. The solid was separated by filtration, washed with isopropanol and dried to provide 1-[2-(4-methoxyphenyl)ethyl]-1H-imidazo[4,5-c]quinoline hydrochloride hydrate, m.p. 209°-213° C. Analysis: Calculated for C19H17N3O.HCl.1/3H2O: %C, 66.0; %H, 5.4; %N, 12.2; Found: %C, 66.1; %H, 5.3; %N, 12.3.

Workup

  1. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-e93a0b0071c944ac9058d34736026049
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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