7-Azido-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile → HCID 21956473, compound

HRID 989300Notes

Reaction equation

HRID 989300 reaction equation
[N:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:16][C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)=[C:9]([C:14]#[N:15])[CH:10]=[N:11]2)=[CH:6][C:5]=1[N+:29]([O-])=O)=[N+]=[N-]>C1COCC1.C(O)C.[Pd]>[NH2:29][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:4]=1[NH2:1])[N:11]=[CH:10][C:9]([C:14]#[N:15])=[C:8]2[NH:16][C:17]1[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=1

Participants

5

Reactant 1

HCID 219564987-Azido-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile

Product 1

HCID 21956473HCID 21956473, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 493.4 mg (1.17 mmol) of 7-azido-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile in 15 mL of THF and 5 mL of ethanol is hydrogenated at 30 psi for 1 hour in the presence of 100.0 mg of 10% palladium-on-carbon. The catalyst is removed by filtration and the solvent removed in vacuo to give 422.1 mg (98.8%) of 6,7-diamino-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile as a deep yellow solid which is used directly in the next step.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0652040f68a5487b839b85b00e7205c1
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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