HCID 22139679, compound → HCID 22139705, compound

HRID 1825866Notes

Reaction equation

HRID 1825866 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-8b615279daa34dde8075b7616af54c9d
Source dataset
uspto-grants-2006_05
Patent number
US07049325B2

Reaction notes

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