Stannous Chloride → 5-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one

HRID 1037759Notes

Reaction equation

HRID 1037759 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:15]([O-])=O)[C:6]1=[O:18].[Sn](Cl)Cl>C1COCC1>[NH2:15][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]=[CH:14][N:5]([CH2:4][CH2:3][N:2]([CH3:19])[CH3:1])[C:6]2=[O:18]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 595792672-(2-Dimethylamino-ethyl)-5-nitro-2H-isoquinolin-1-one

Product 1

HCID 595794535-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Dimethylamino-ethyl)-5-nitro-2H-isoquinolin-1-one (0.67 g, 2.6 mmol) and dehydrate tin dichloride (2 g, 10 mml) were stirred in THF (10 mL) at room temperature for 24 hours. The volatiles were removed via rotovapor, and the residue was dissolved in CH2Cl2 (1 L), washed with aqueous saturated NaHCO3 solution (30 mL×3). The organic layer was dried over Na2SO4, filtered and concentrated to dryness gave 5-Amino-2-(2-dimethylamino-ethyl)-2H-isoquinolin-1-one as a yellow solid. The compound was used for next steps without further purification.

Workup

  1. customThe volatiles were removed via rotovapor
  2. dissolutionthe residue was dissolved in CH2Cl2 (1 L)
  3. washwashed with aqueous saturated NaHCO3 solution (30 mL×3)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b77dc1712f8e4d5ca9009d9e2cc01e18
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

Loading…