Stannous chloride dihydrate → HCID 59427335, compound

HRID 503566Notes

Reaction equation

HRID 503566 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH:13]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)O)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.O.O.[Sn](Cl)Cl>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:13][C:15]3[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrate2×HCID 59427359HCID 59427359, compound

Product 1

HCID 59427335HCID 59427335, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (7-methoxyquinolin-4-yl)(4-nitrophenyl)methanol (0.187 g, 0.603 mmol) and tin(II) chloride dihydrate (0.823 g, 3.62 mmol) in MeOH (10 mL) was heated to 60° C. After 1 hr, an additional 5 eq of tin(II) chloride dihydrate was added. After 3 hrs, the mixture was concentrated in vacuo and diluted with EtOAc and water. Saturated NaHCO3 was added until the aqueous layer was basic. The resulting suspension was filtered and the solids washed with EtOAc. The organic fraction was washed with water and brine. After drying with Na2SO4 and concentrating in vacuo, the crude yellow solid, 4-((7-methoxyquinolin-4-yl)methyl)benzenamine was advanced without further purification. [email protected] min.

Workup

  1. waitAfter 3 hrs
  2. concentrationthe mixture was concentrated in vacuo
  3. additiondiluted with EtOAc and water
  4. additionSaturated NaHCO3 was added until the aqueous layer
  5. filtrationThe resulting suspension was filtered
  6. washthe solids washed with EtOAc
  7. washThe organic fraction was washed with water and brine
  8. dry with materialAfter drying with Na2SO4
  9. concentrationconcentrating in vacuo
  10. customthe crude yellow solid, 4-((7-methoxyquinolin-4-yl)methyl)benzenamine was advanced without further purification
  11. custom[email protected] min.

Sources & evidence

ORD record
ord-fcea2297aa4e4c509a98c9b77f97525c
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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