Hydrochloric Acid → HCID 58934068, compound

HRID 2102775Notes

Reaction equation

HRID 2102775 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[C:18]([CH2:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:17]([N+:30]([O-])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn].Cl.C([O-])(O)=O.[Na+]>CO>[NH2:30][C:17]1[C:18]([CH2:20][S:21]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)(=[O:23])=[O:22])=[N:19][C:14]([N:11]2[CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][CH2:12]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5352426Tin atomHCID 58934064HCID 58934064, compound

Product 1

HCID 58934068HCID 58934068, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of 6-(4-benzylpiperazin-1-yl)-3-nitro-2-[(phenylsulfonyl)-methyl]pyridine (1.81 g, 4.00 mmol) and granular tin (2.09 g, 17.6 mmol) in methanol is treated with conc. HCl, heated under nitrogen at 50° C. for 7 h, stirred at ambient temperatures for 16 h, poured into aqueous NaHCO3 and extracted with EtOAc. The combined extracts are dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, EtOAc as eluent) to afford the title compound as a yellow solid, 1.47 g (87% yield), mp 175-176° C., identified by NMR and mass spectral analyses.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined extracts are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue is chromatographed (silica gel, EtOAc as eluent)

Sources & evidence

ORD record
ord-2529d790cadb4d0cb7f61511cea5cdf7
Source dataset
uspto-grants-2009_08
Patent number
US07576087B2

Reaction notes

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