Acetic Acid → 6-Amino-4-(3-chloro-4-fluroanilino)-7-(4-methyl-1-piperazinyl)-3-quinolinecarbonitrile

HRID 548502Notes

Reaction equation

HRID 548502 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[C:13]([N+:16]([O-])=O)[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:26]#[N:27].C(O)(=O)C>CO.[Fe]>[NH2:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[N:19]1[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]1)[N:9]=[CH:8][C:7]([C:26]#[N:27])=[C:6]2[NH:5][C:4]1[CH:28]=[CH:29][C:30]([F:31])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 216973254-(3-Chloro-4-fluoroanilino)-7-(4-methyl-1-piperazinyl)-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 216972946-Amino-4-(3-chloro-4-fluroanilino)-7-(4-methyl-1-piperazinyl)-3-quinolinecarbonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

In the manner of Example 23 4-(3-chloro-4-fluoroanilino)-7-(4-methyl-1-piperazinyl)-6-nitro-3-quinolinecarbonitrile was reduced with iron powder and acetic acid in MeOH to give the title compound as an amorphous solid; ms 411.2 (M+H)+, 206.2 (M+2H)+2.

Sources & evidence

ORD record
ord-4cace6bee5864309b12afa4f1622b976
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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