Sodium Chloride → HCID 21846914, compound

HRID 619735Notes

Reaction equation

HRID 619735 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([S:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]=[CH:21]3)[CH:12]=[CH:11][C:10]=1[N+:26]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Na+]>Cl>[CH2:1]([NH:8][C:9]1[C:10]([NH2:26])=[CH:11][CH:12]=[C:13]([S:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]=[CH:21]3)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 21846926HCID 21846926, compound

Product 1

HCID 21846914HCID 21846914, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N1-Benzyl-5-(5-isoquinolylsulfanyl)-2-nitroaniline 840 mg (2.2 mmol) was dissolved in concentrated hydrochloric acid 25 ml, stannous chloride dihydrate 2.45 g (10.8 mmol) was added, and the mixture was stirred overnight at room temperature. 50% sodium chloride was added to obtain an alkaline solution, and the solution was extracted with ethyl acetate. The organic layer was washed with water and with saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and N2-benzyl-4-(5-isoquinolylsulfanyl)-1,2-benzene diamine 730 mg (94.1%) was obtained.

Workup

  1. customto obtain an alkaline solution
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water and with saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-291ca5ba0e424df1bb5a726137baad77
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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