Sodium Hydroxide → HCID 23112159, compound

HRID 1373068Notes

Reaction equation

HRID 1373068 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[C:5]([CH:15]=[CH2:16])=[CH:4][N:3]=1.[OH-].[Na+]>C(OCC)(=O)C>[NH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[C:5]([CH:15]=[CH2:16])=[CH:4][N:3]=[C:2]2[Cl:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23112177HCID 23112177, compound

Product 1

HCID 23112159HCID 23112159, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The 1-chloro-5-nitro-4-vinylisoquinoline (15 g) obtained in Step C mentioned above was dissolved in ethyl acetate (700 ml), added with stannous chloride dihydrate (72 g), and stirred for two hours. The reaction mixture was poured on ice, and then added with 5 N aqueous sodium hydroxide. The organic layer was separated, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (10 g).

Workup

  1. additionThe reaction mixture was poured on ice
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-651516ff71d84f6ba224296bec61c090
Source dataset
uspto-grants-2007_01
Patent number
US07160894B2

Reaction notes

Loading…