Stannous chloride dihydrate → HCID 59427335, compound

HRID 1013704Notes

Reaction equation

HRID 1013704 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, brine, and dried with Na2SO4. After concentrating in vacuo, the crude, yellow solid, 4-((7-methoxyquinolin-4-yl)methyl)benzenamine was advanced without further purification. MS found: M+H+=265.1.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additiondiluted with EtOAc and water
  3. additionSaturated NaHCO3 was added until the aqueous layer
  4. filtrationThe resulting suspension was filtered
  5. washthe solids washed with EtOAc
  6. washThe organic fraction was washed with water, brine
  7. dry with materialdried with Na2SO4
  8. concentrationAfter concentrating in vacuo
  9. customthe crude, yellow solid, 4-((7-methoxyquinolin-4-yl)methyl)benzenamine was advanced without further purification

Sources & evidence

ORD record
ord-362611cf3b654dff811fffa516f2894f
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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