7-Azido-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrile → 6,7-Diamino-4-(5-methoxy-2-methylanilino)-3-quinolinecarbonitrile

HRID 989296Notes

Reaction equation

HRID 989296 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])[CH:20]=[CH:19][C:18]=3[CH3:25])=[C:9]([C:14]#[N:15])[CH:10]=[N:11]2)=[CH:6][C:5]=1[N+:26]([O-])=O)=[N+]=[N-].[H][H]>[Pd].C(O)C.O1CCCC1>[NH2:26][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:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[CH3:25]

Participants

5

Reactant 2

HCID 219564947-Azido-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 219563956,7-Diamino-4-(5-methoxy-2-methylanilino)-3-quinolinecarbonitrileYield 72.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of 0.65 g (1.73 mmol ) of 7-azido-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrile and 0.12 g of 10% palladium on carbon in a 1:1 mixture of ethanol/tetrahydrofuran is shaken on Parr apparatus with hydrogen gas at 40 psi for 2 hours. The mixture is filtered through a pad of diatomaceous earth, washed with methanol and tetrahydrofuran, then dried to provide a dark solid. The crude product is purified by silica gel chromatography, utilizing a gradient of methylene chloride/methanol (95:5 to 88:12) to yield 0.4 g of 6,7-diamino-4-(5-methoxy-2-methylanilino)-3-quinolinecarbonitrile as a dark solid, mp 245° C. (dec).

Workup

  1. filtrationThe mixture is filtered through a pad of diatomaceous earth
  2. washwashed with methanol and tetrahydrofuran
  3. customdried
  4. customto provide a dark solid
  5. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-f7d2c4fa4a364c0eada66e8d5f8e92e0
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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