Water → o-Amino-N-(2-chloro-3-pyridyl)benzamide

HRID 1258039Notes

Reaction equation

HRID 1258039 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[C:6]([NH:8][C:9]1[C:10]([Cl:15])=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:7])([O-])=O.O.[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[C:6]([NH:8][C:9]1[C:10]([Cl:15])=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70570n-(2-Chloropyridin-3-yl)-2-nitrobenzamide

Product 1

HCID 70389o-Amino-N-(2-chloro-3-pyridyl)benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stannous chloride (60.0 g, 320 mmol) was added in the solution of 2-nitro-N-(2-chloro-pyridin-3-yl)-benzamide (14.0 g) in absolute ethanol (200 mL). After being refluxed for 4 hours the solution was diluted with 160 ml conc. HCI and left in the refrigerator to crystallize. Obtained product was isolated by filtration. Isolated substance was dissolved in 100 ml boiling water and made alkaline with 30% NaOH (pH 8.5). Obtained precipitate was isolated by filtration and dried. Yield 7.0 g, mp 172-175° C.

Workup

  1. temperatureAfter being refluxed for 4 hours the solution
  2. additionwas diluted with 160 ml conc. HCI
  3. waitleft in the refrigerator
  4. customto crystallize
  5. customObtained product was isolated by filtration
  6. customIsolated substance
  7. dissolutionwas dissolved in 100 ml
  8. customObtained precipitate
  9. customwas isolated by filtration
  10. customdried

Sources & evidence

ORD record
ord-3a82e54917a5416693f706ff0e693f90
Source dataset
uspto-grants-2013_06
Patent number
US08466144B2

Reaction notes

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