Triethylamine → HCID 20183629, compound

HRID 255535Notes

Reaction equation

HRID 255535 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1.C(N(CC)CC)C>CN(C)C=O>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:20][CH:21]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 145334-Aminophenylacetic acidHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 20183629HCID 20183629, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using the method of Example 1, 4-chloro-3-nitroquinoline was reacted with 4-aminophenylacetic acid in N,N-dimethylformamide in the presence of triethylamine to provide N-(3-nitro-4-quinolinyl)-4-aminophenylacetic acid. This acid was reduced using the method of Example 26 to provide N-(3-amino-4-quinolinyl)-4-aminophenylacetic acid. This diamine was then reacted with formic acid using the method of Example 137 to provide 1-(4-carboxymethylphenyl)-1H-imidazo[4,5-c]quinoline. Recrystallization from methanol provided solid of m.p. 236°-240° C. Analysis: Calculated for C18H13N3O2 : %C, 71.3; %H, 4.3; %N, 13.9; Found; %C, 70.8; %H, 4.3; %N, 13.7.

Sources & evidence

ORD record
ord-64f16bdff78541cf848bbcca52762288
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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