Ammonium Chloride → HCID 11739339, compound

HRID 2086065Notes

Reaction equation

HRID 2086065 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:21]([O-])=O)[C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:10]=2)=[N:6][CH:7]=1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[Cl-].[NH4+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([NH2:21])[C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 73972Sodium sulfide nonahydrateHCID 22727956HCID 22727956, compound

Product 1

HCID 11739339HCID 11739339, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of N-(5-bromo-3-nitropyridin-2-yl)-N-[3-(pyridin-3-yl)phenyl]amine (3.7 g, 10 mmol), sodium sulphide nonahydrate (7.2 g, 30 mmol) and ammonium chloride (1.6 g, 30 mmol) in methanol (15 ml) was heated under reflux for 90 minutes. The reaction was cooled, evaporated to dryness and the residue suspended in ethyl acetate (200 ml). This was washed with water, brine, dried over anhydrous sodium sulphate, filtered and evaporated to dryness to afford 5-bromo-N2-[3-(pyridin-3-yl)phenyl]-pyridine-2,3-diamine as a yellow oil (3.4 g, 100%) which was used without purification; m/z (ES+) 341 and 343 (M++H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 90 minutes
  3. temperatureThe reaction was cooled
  4. customevaporated to dryness
  5. washThis was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-fbf165b40e72454097b6cd174f757fab
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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