(6-nitro-quinolin-2-yl)-(R)-indan-1-yl-amine → (R)-N2-Indan-1-yl-quinoline-2,6-diamine

HRID 1928711Notes

Reaction equation

HRID 1928711 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:21]([O-])=O)[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>C(OCC)(=O)C.[Pd]>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57860965(6-nitro-quinolin-2-yl)-(R)-indan-1-yl-amine

Product 1

HCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(R)-Indan-1-yl-(6-nitro-quinolin-2-yl)-amine (1.5 g, 5.0 mmol) were dissolved in ethyl acetate (60 mL). Upon addition of palladium on carbon (10%) the reaction mixture was stirred for 2 h at ambient temperature under an atmosphere of hydrogen. Then the catalyst was filtered off, the filter washed with ethyl acetate and the filtrate evaporated. (R)—N2-Indan-1-yl-quinoline-2,6-diamine was obtained as a yellow foam (1.3 g, 96%); MS: m/e=276.4 (M+H+).

Workup

  1. filtrationThen the catalyst was filtered off
  2. washthe filter washed with ethyl acetate
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-7b5394ddfb5941f0be58805d2f052ce4
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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