Hydrazine → 4-(7-(Benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorobenzenamine

HRID 1993391Notes

Reaction equation

HRID 1993391 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:21]=3[F:29])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C1COCC1.[Ni]>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=3[F:29])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 229354107-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline

Product 1

HCID 597920394-(7-(Benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorobenzenamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 7-(benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline (Step 1, 4.5 g, 10.7 mmol) and hydrazine (2 mL, 61 mmol) in THF (200 mL) was added Raney 2400 nickel (1 mL slurry in water). The suspension was stirred for 30 min. The mixture was filtered through a bed of Celite®, then solvents were removed under reduced pressure to afford the title compound. Calc'd Mass for C23H19FN2O3, 390, MS (M+1) 391.

Workup

  1. filtrationThe mixture was filtered through a bed of Celite®
  2. customsolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-cff1021a90aa41a7bf576371a629e613
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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