Sodium Hydroxide → 4-Fluoro-5-(5-isoquinolylsulfanyl)-1,2-benzenediamine

HRID 619728Notes

Reaction equation

HRID 619728 reaction equation
[F:1][C:2]1[C:8]([S:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][N:14]=[CH:15]3)=[CH:7][C:5]([NH2:6])=[C:4]([N+:20]([O-])=O)[CH:3]=1.[OH-].[Na+]>Cl>[F:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]([NH2:6])=[CH:7][C:8]=1[S:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][N:14]=[CH:15]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 218469024-Fluoro-5-(5-isoquinolylsulfanyl)-2-nitroaniline

Product 1

HCID 218469084-Fluoro-5-(5-isoquinolylsulfanyl)-1,2-benzenediamineYield 69.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-Fluoro-5-(5-isoquinolylsulfanyl)-2-nitroaniline 1.60 g (5.1 mmol) was dissolved in concentrated hydrochloric acid 30 ml, stannous chloride dihydrate 4.10 g (18.2 mmol) was added, and the mixture was stirred for 2 hours at room temperature. After 50% sodium hydroxide was added, the resulting alkaline solution was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate-n-hexane to obtain 4-fluoro-5-(5-isoquinolylsulfanyl)-1,2-benzenediamine 1.00 g (69.1%).

Workup

  1. extractionthe resulting alkaline solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-14812b6731cd4dd38003d72eb9372e25
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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