4-chloro-3-nitro-N-(pyridin-3-ylmethyl)benzenesulfonamide → 4-Amino-3-nitro-N-(3-pyridinylmethyl)benzenesulfonamide

HRID 2099848Notes

Reaction equation

HRID 2099848 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[NH3:22].CO>>[NH2:22][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

3

Reactant 2

HCID 28583054-chloro-3-nitro-N-(pyridin-3-ylmethyl)benzenesulfonamideHCID 21705897Ammonia methanol

Product 1

HCID 222851684-Amino-3-nitro-N-(3-pyridinylmethyl)benzenesulfonamide

Conditions

Temperature
100 °C

Procedure

Into a saturated ammonia-methanol solution (60 ml) was added 4-chloro-3-nitro-N-(pyridin-3-ylmethyl)benzenesulfonamide (2.77 g), followed by about 2 days of heating at 100° C. in a sealed tube. After the reaction, the solvent was evaporated under reduced pressure and the formed yellow crystals were collected by filtration and dried to obtain 4-amino-3-nitro-N-(pyridin-3-ylmethyl)benzenesulfonamide (2.51 g). Hereinafter, the compound of Reference Examples 26 was obtained similarly.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. filtrationthe formed yellow crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-80a05f61f7974e20b26e77a75147fa75
Source dataset
uspto-grants-2009_08
Patent number
US07569688B2

Reaction notes

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