HCID 22139679, compound → HCID 22139705, compound

HRID 456997Notes

Reaction equation

HRID 456997 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([N+:17]([O-])=O)=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2.[PH2]([O-])=O.[Na+]>C1COCC1>[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([NH2:17])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

4

Reactant 2

HCID 22139679HCID 22139679, compoundHCID 178527019HCID 178527019, compound

Product 1

HCID 22139705HCID 22139705, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2,4-difluoro-phenoxy)-6-methoxy-8-nitro-quinoline (1.36 g, 4.1 mmol) in 30 mL of THF was added an aqueous solution of sodium hypophosphite (2.7 g, 31 mmol in 10 mL H2O). The reaction mixture was degassed under N2, treated with Pd/C (˜1 g), and stirred at room temperature under N2 for 1 hour. The reaction mixture was filtered through Celite®, and washed with 1N NaOH solution followed by water. The organic layer was dried over MgSO4, and the solvent removed to give 0.9 g (75%) of 5-(2,4-difluoro-phenoxy)-6-methoxy-quinolin-8-ylamine.

Workup

  1. customThe reaction mixture was degassed under N2
  2. additiontreated with Pd/C (˜1 g)
  3. filtrationThe reaction mixture was filtered through Celite®
  4. washwashed with 1N NaOH solution
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent removed

Sources & evidence

ORD record
ord-fea57a8244fe49c5bc05ff48daf7f1d4
Source dataset
uspto-grants-2007_03
Patent number
US07186840B2

Reaction notes

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