Acetic Acid → HCID 69043488, compound

HRID 397946Notes

Reaction equation

HRID 397946 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]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]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH:26]=1)=[O:16])[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 113598-AminoquinolineHCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetate

Product 1

HCID 69043488HCID 69043488, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 384, 8-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 light brown crystalline solid. Mp.>92° C. dec. (AcOEt/hexane), MS: m/e=267 (M+).

Sources & evidence

ORD record
ord-544b84ec6fe0418eafeac21ae243b2be
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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