Water → HCID 85969746, compound

HRID 1916621Notes

Reaction equation

HRID 1916621 reaction equation
O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+].[CH3:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:15][C:14]=1[N+:25]([O-])=O.O>CCOC(C)=O.OS([O-])(=O)=O.[K+]>[CH3:11][NH:12][C:13]1[C:14]([NH2:25])=[CH:15][C:16]([CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 62177350HCID 62177350, compound

Product 1

HCID 85969746HCID 85969746, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516920Potassium bisulfateSolvent

Procedure

4.85 g (21.5 mmol) tin(II)chloride dihydrate and 4.45 g (53.0 mmol) NaHCO3 are added to a solution of 1.00 g (4.25 mmol) methyl-(2-nitro-4-pyrrolidin-1-ylmethyl-phenyl)-amine in 60 mL EtOAc at RT. The reaction is refluxed for 2 h and then diluted with 100 mL 1 M KHSO4 solution and some water. The mixture is filtered. The aqueous phase is combined with K2CO3 and extracted twice with 80 mL EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac.

Workup

  1. temperatureThe reaction is refluxed for 2 h
  2. filtrationThe mixture is filtered
  3. extractionextracted twice with 80 mL EtOAc
  4. dry with materialThe organic phase is dried over MgSO4

Sources & evidence

ORD record
ord-bb4a24ea055c4c6193ded6bd577d44aa
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…