Methyl 4-(2-nitropyridin-3-ylthio)benzoate → Methyl 4-(2-aminopyridin-3-ylthio)benzoate

HRID 1806111Notes

Reaction equation

HRID 1806111 reaction equation
[N+:1]([C:4]1[C:9]([S:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1)([O-])=O>C(O)(=O)C.ClCCl.[Zn]>[NH2:1][C:4]1[C:9]([S:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 1

HCID 66995042Methyl 4-(2-nitropyridin-3-ylthio)benzoate

Product 1

HCID 66994709Methyl 4-(2-aminopyridin-3-ylthio)benzoateYield 99.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Added zinc powder (13.88 g, 212.2 mmol) slowly to a solution of methyl 4-(2-nitropyridin-3-ylthio)benzoate (6.16 g, 21.22 mmol) in acetic acid (75 mL) at ambient temperature in an ambient water bath. Stirred for an hour, diluted with dichloromethane, and filtered through celite. Washed the celite pad several times with dichloromethane. Concentrated the filtrate, and partitioned the residue between 2N NaOH and ethyl acetate. The organic layer was washed with water, brine, dried and concentrated to afford the title compound (5.5 g, 99.57% yield).

Workup

  1. filtrationfiltered through celite
  2. washWashed the celite pad several times with dichloromethane
  3. concentrationConcentrated the filtrate
  4. custompartitioned the residue between 2N NaOH and ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-90927b1569c64d86b532574896dd6627
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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