(2-Methoxy-benzyl)-(6-nitro-quinolin-2-yl)-amine → N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine

HRID 1803075Notes

Reaction equation

HRID 1803075 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:17]([O-])=O)[CH:13]=2)[N:8]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=2)[N:8]=1

Participants

4

Reactant 1

HCID 57647540(2-Methoxy-benzyl)-(6-nitro-quinolin-2-yl)-amine

Product 1

HCID 43450845N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(2-Methoxy-benzyl)-(6-nitro-quinolin-2-yl)-amine (0.5 g, 2.0 mmol) were dissolved in ethyl acetate (25 ml). Upon addition of Pd/C (10%, 0.1 g) the reaction mixture was stirred for 45 min at ambient temperature under an atmosphere of hydrogen. Then the catalyst was filtered off, the filter washed with ethyl acetate and the filtrate evaporated. N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine was obtained as a yellow foam (0.40 g, 87%); MS: m/e=280.5 (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-2fbd740fd08441269def9e08f5e5e17a
Source dataset
uspto-grants-2013_01
Patent number
US08350028B2

Reaction notes

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