Tin atom → 3-Amino-6-methoxy-2-[(phenylsulfonyl)methyl]-pyridine

HRID 1791149Notes

Reaction equation

HRID 1791149 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:6]([N+:19]([O-])=O)=[CH:5][CH:4]=1.[Sn]>CO.Cl>[NH2:19][C:6]1[C:7]([CH2:9][S:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)(=[O:12])=[O:11])=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 5352426Tin atomHCID 13902761(6-Methoxy-3-nitro-2-pyridinyl)methyl phenyl sulfone

Product 1

HCID 220281923-Amino-6-methoxy-2-[(phenylsulfonyl)methyl]-pyridineYield 94.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 6-methoxy-3-nitro-2-[(phenylsulfonyl)methyl]-pyridine (6.17 g, 20.0 mmol) in methanol and concentrated HCl (50 mL) is treated with thin strips of tin foil (10.0 g, 84.2 mmol), heated at 60° C. for 20 h, and filtered hot. The filtrate is poured over ice and 2.5N aqueous NaOH, stirred for 0.5 h and filtered. The filtercake is air-dried to afford the title compound as a white solid 5.26 g (94% yield), identified by mass spectral and HNMR analyses.

Workup

  1. filtrationfiltered hot
  2. additionThe filtrate is poured over ice and 2.5N aqueous NaOH
  3. filtrationfiltered
  4. customThe filtercake is air-dried

Sources & evidence

ORD record
ord-0eb85c8880e1422abb387eb3d19ab874
Source dataset
uspto-grants-2006_07
Patent number
US07074792B2

Reaction notes

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