7-Azido-6-nitro-4-(4-phenoxyanilino)-3-quinolinecarbonitrile → 6,7-Diamino-4-(4-phenoxyanilino)-3-quinolinecarbonitrile

HRID 2213743Notes

Reaction equation

HRID 2213743 reaction equation
NC1C=C2C(=CC=1N)N=CC(C#N)=C2NC1C=C(OC)C(OC)=C(OC)C=1.[N:28]([C:31]1[CH:40]=[C:39]2[C:34]([C:35]([NH:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[CH:46][CH:45]=3)=[C:36]([C:41]#[N:42])[CH:37]=[N:38]2)=[CH:33][C:32]=1[N+:57]([O-])=O)=[N+]=[N-]>C1COCC1.C(O)C.[Pd]>[NH2:57][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][C:31]=1[NH2:28])[N:38]=[CH:37][C:36]([C:41]#[N:42])=[C:35]2[NH:43][C:44]1[CH:45]=[CH:46][C:47]([O:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)=[CH:48][CH:49]=1

Participants

6

Reactant 2

HCID 219564597-Azido-6-nitro-4-(4-phenoxyanilino)-3-quinolinecarbonitrileHCID 21956473HCID 21956473, compound

Product 1

HCID 219564666,7-Diamino-4-(4-phenoxyanilino)-3-quinolinecarbonitrileYield 119.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure of 6,7-diamino-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile (intermediate from Example 33), hydrogenation of a suspension of 736.0 mg (1.74 mmol) of 7-azido-6-nitro-4-(4-phenoxyanilino)-3-quinolinecarbonitrile and 147.2 mg of 10% palladium-on-carbon in 21 mL of THF and 6 mL of ethanol yields 765.1 mg of crude 6,7-diamino-4-(4-phenoxyanilino)-3-quinolinecarbonitrile.

Sources & evidence

ORD record
ord-54f586a5679a474f838e1ba15c791474
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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