(2-Methoxy-benzyl)-[5-((E)-styryl)-quinolin-2-yl]-amine → (2-Methoxy-benzyl)-(5-phenethyl-quinolin-2-yl)-amine

HRID 1170074Notes

Reaction equation

HRID 1170074 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]=1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:8]=1

Participants

5

Reactant 2

HCID 68433914(2-Methoxy-benzyl)-[5-((E)-styryl)-quinolin-2-yl]-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 68435900(2-Methoxy-benzyl)-(5-phenethyl-quinolin-2-yl)-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2-Methoxy-benzyl)-[5-((E)-styryl)-quinolin-2-yl]-amine (example 2, 102 mg, 0.279 mmol) was dissolved in 20 mL ethanol. Palladium on charcoal (10%, 30 mg, 0.028 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 light brown oil (97 mg, 95%), MS: m/e=369.0 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-709e5e2f70ac44cd9fde57de62aa2407
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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