Stannous chloride dihydrate → (4-Amino-3-methylphenyl)(1-methyl-1H-imidazol-5-yl)methanone

HRID 928781Notes

Reaction equation

HRID 928781 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([CH3:18])[CH:10]=2)=[O:8])=[CH:5][N:4]=[CH:3]1.O.O.[Sn](Cl)Cl>CCO>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]([C:6]2[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=2)=[O:8])=[CH:10][C:11]=1[CH3:18]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 86715615(1-Methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone2×

Product 1

HCID 86715616(4-Amino-3-methylphenyl)(1-methyl-1H-imidazol-5-yl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1-methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone (3.3 g, 13.456 mmol, Intermediate 40: step b) and tin(II)chloride dihydrate (15.6 g, 67.282 mmol) in EtOH (80 mL) was stirred at reflux for 1 hour, cooled to room temperature overnight and evaporated in vacuo to remove most of the EtOH. The residue was poured into a 3M aqueous NaOH/ice solution rinsing with EtOAc. The mixture was stirred at room temperature for 15 minutes and layers were separated. The aqueous layer was again extracted with EtOAc. The combined EtOAc extracts were washed with brine, dried (Na2SO4), filtered, and evaporated in vacuo to provide crude product. The tan solid title compound was precipitated from Et2O, collected by filtration and dried.

Workup

  1. temperatureat reflux for 1 hour
  2. customevaporated in vacuo
  3. customto remove most of the EtOH
  4. additionThe residue was poured into a 3M aqueous NaOH/ice solution
  5. washrinsing with EtOAc
  6. stirringThe mixture was stirred at room temperature for 15 minutes
  7. customlayers were separated
  8. extractionThe aqueous layer was again extracted with EtOAc
  9. washThe combined EtOAc extracts were washed with brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated in vacuo
  13. customto provide crude product
  14. customThe tan solid title compound was precipitated from Et2O
  15. filtrationcollected by filtration
  16. customdried

Sources & evidence

ORD record
ord-7d01e6eff5464744983ae78b4997fb31
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

Loading…