Acetic Acid → HCID 69042755, compound

HRID 433641Notes

Reaction equation

HRID 433641 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH:12]([O:19][CH2:20][CH3:21])([O:16]CC)OCC.[N+:22]([CH2:25][C:26](OCC)=O)([O-])=O.[C:31](O)(=O)C>[Fe]>[CH2:20]([O:19][C:12]([C:25]1[N:22]=[CH:31][N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][CH:6]=[CH:5]3)[CH:26]=1)=[O:16])[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 113736-AminoquinolineHCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetate

Product 1

HCID 69042755HCID 69042755, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 384, 6-aminoquinoline was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid. After workup and chromatography the title compound was obtained as a brown crystalline solid. Mp. 90-94° C. (AcOEt hexane), MS: m/e=268 (M+H+).

Sources & evidence

ORD record
ord-df0d60fcec7a4dcba95bb2ddfe690427
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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