(R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amine → (R)-N2-Indan-1-yl-quinoline-2,5-diamine

HRID 1671552Notes

Reaction equation

HRID 1671552 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[N+:21]([O-])=O)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H][H]>C(O)C.[Pd]>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([NH2:21])=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 67096022(R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 44219082(R)-N2-Indan-1-yl-quinoline-2,5-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amine (2.66 g, 8.7 mmol) was dissolved in 420 mL ethanol. Palladium on charcoal (10%, 463 mg, 0.4 mmol) was added and the reaction mixture war hydrogenated with a hydrogen balloon overnight. The palladium was filtered off and the solvent was evaporated. The title compound was obtained as a brown solid (2.29 g, 95%), MS: m/e=276.3 (M+H+).

Workup

  1. filtrationThe palladium was filtered off
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9640605f56da41fca579637f2b8d52f3
Source dataset
uspto-grants-2011_08
Patent number
US07994324B2

Reaction notes

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