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

HRID 911864Notes

Reaction equation

HRID 911864 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-8c32ef8a3cb54c7b8698674ac93061a5
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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