(3-Methylsulfanylpropyl)-(3-nitro-7-phenylquinolin-4-yl)amine → N4-(3-methylsulfanylpropyl)-7-phenylquinoline-3,4-diamine

HRID 1818114Notes

Reaction equation

HRID 1818114 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[N+:23]([O-])=O>C1(C)C=CC=CC=1.[Pt]>[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[NH2:23]

Participants

4

Reactant 1

HCID 21984176(3-Methylsulfanylpropyl)-(3-nitro-7-phenylquinolin-4-yl)amine

Product 1

HCID 86593757N4-(3-methylsulfanylpropyl)-7-phenylquinoline-3,4-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

(3-Methylsulfanylpropyl)-(3-nitro-7-phenylquinolin-4-yl)amine (3.0 g, 8.5 mmol) was hydrogenated in a Parr bottle over Pt/C (0.3 g of 5%) in 42 mL of toluene for 1 h. The reaction mixture was filtered through CELITE filter agent, washed with methanol (100 mL) and CHCl3 (50 mL), and then concentrated to afford 2.75 g of N4-(3-methylsulfanylpropyl)-7-phenylquinoline-3,4-diamine as a brown oil.

Workup

  1. filtrationThe reaction mixture was filtered through CELITE
  2. filtrationfilter agent
  3. washwashed with methanol (100 mL) and CHCl3 (50 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3673e675efa64b80b475d70ff6ad7fdd
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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