Stannous chloride dihydrate → HCID 23139425, compound

HRID 919496Notes

Reaction equation

HRID 919496 reaction equation
O.O.Cl[Sn]Cl.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=1[C:17]1[N:21]([CH3:22])[N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1>CCO>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[C:17]1[N:21]([CH3:22])[N:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 23139423HCID 23139423, compound

Product 1

HCID 23139425HCID 23139425, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

SnCl2.2H2O (0.15 g, 0.66 mmol, 4.0 eq.) was added to a stirred solution of 5-(2-methoxy-5-nitro-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole, see Example 1.99, (0.05 g, 0.16 mmol) in EtOH (2.0 mL). The mixture was stirred at reflux for 4 hrs and EtOH was removed under vacuum. The resulting solid was dissolved in EtOAc and 1N NaOH was added until the pH was adjusted to 6. The mixture was stirred overnight and filtered through celite. The aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phase was dried over anhydrous MgSO4, filtered and evaporated to give 4-methoxy-3-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-phenylamine (0.04 g, 0.15 mmol, 97% yield): LCMS m/z (%)=272 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ: 6.82 (dd, J=16.0, 4.0 Hz, 1H), 6.79 (dd, J=10.0, 2.0 Hz, 1H), 6.61 (d, 1H), 6.46 (s, 1H), 3.76 (s, 3H), 3.74 (s, 3H).

Workup

  1. temperatureat reflux for 4 hrs
  2. customEtOH was removed under vacuum
  3. dissolutionThe resulting solid was dissolved in EtOAc
  4. addition1N NaOH was added until the pH
  5. stirringThe mixture was stirred overnight
  6. filtrationfiltered through celite
  7. extractionThe aqueous phase was extracted with EtOAc (3×50 mL)
  8. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-fae022fb3c9e4e9b90fb8d17023afd52
Source dataset
uspto-grants-2016_03
Patent number
US09273035B2

Reaction notes

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