Stannous chloride dihydrate → HCID 23139425, compound

HRID 540581Notes

Reaction equation

HRID 540581 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-c65493e890c74fd9bb6254428aaaf896
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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