Sodium Hydroxide → 4-[(4-Amino-2-bromophenylthio)methyl]pyridine

HRID 617738Notes

Reaction equation

HRID 617738 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[S:11][CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C.Cl.O>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:2]([Br:1])[CH:7]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 218496744-[(2-Bromo-4-nitrophenylthio)methyl]pyridine

Product 1

HCID 218496814-[(4-Amino-2-bromophenylthio)methyl]pyridine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-[(2-Bromo-4-nitrophenylthio)methyl]pyridine (D14) (0.800 g, 2.56 mmol) was dissolved in ethanol (40 ml) and heated to 60° C. with stifling. A solution of tin (II) chloride (1.696 g, 8.96 mmol) in conc. HCl (8 ml) was then added dropwise. The reaction mixture was heated under reflux for 2 h, then allowed to cool, diluted with water (40 ml) and basified to pH14 by the addition of 10% sodium hydroxide. The reaction mixture was concentrated in vacuo and the aqueous residue was extracted with dichloromethane (2×70 ml). The combined organic layers were then dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a brown oil, which was dried in vacuo (0.670 g, 93%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureto cool
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. extractionthe aqueous residue was extracted with dichloromethane (2×70 ml)
  6. dry with materialThe combined organic layers were then dried (Na2SO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-426e9dd47b264041b0ca1ee14f9789a0
Source dataset
uspto-grants-1999_09
Patent number
US05952325

Reaction notes

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