n-[6-(6,7-Dimethoxy(4-quinolyloxy))(2-naphthyl)](phenylmethoxy)carboxamide → 6-(6,7-Dimethoxy-4-quinolyloxy)-2-naphthylamine

HRID 2115751Notes

Reaction equation

HRID 2115751 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH:26]C(OCC1C=CC=CC=1)=O)[CH:20]=[CH:19]2>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH2:26])[CH:20]=[CH:19]2

Participants

4

Reactant 1

HCID 59813732n-[6-(6,7-Dimethoxy(4-quinolyloxy))(2-naphthyl)](phenylmethoxy)carboxamide

Product 1

HCID 675205556-(6,7-Dimethoxy-4-quinolyloxy)-2-naphthylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[6-(6,7-dimethoxy(4-quinolyloxy))(2-naphthyl)](phenylmethoxy)carboxamide (Step b, 170 mg, 0.35 mmol) and Pd/C (17 mg, 10%, Aldrich) in 60 mL of EtOAc was stirred at RT under H2 balloon for 16 h. The mixture was filtered through a Celite® pad. The filtrate was concentrated in vacuo to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 347.0 (M+1). Mass Calc'd for C21H18N2O3: 346.13.

Workup

  1. filtrationThe mixture was filtered through a Celite® pad
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e9f014b3d8d94dab974e22d735a2cb8a
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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