Sodium borohydride → HCID 58349459, compound

HRID 2090061Notes

Reaction equation

HRID 2090061 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:15])[C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-])=O)[CH:8]=[CH:7][CH:6]=2.[BH4-].[Na+]>O1CCOCC1.CO.O.[Ni](Cl)Cl>[NH2:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([Cl:1])[N:3]=[C:4]2[CH3:15]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 58349453HCID 58349453, compound

Product 1

HCID 58349459HCID 58349459, compound

Reagents, catalysts & solvents 3

HCID 16212333Nickel chloride hydrateCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-chloro-1-methyl-5-nitroisoquinoline (2.0 g, 9.0 mmol) in dioxane (48 mL) and MeOH (10 mL) was added nickel (11) chloride hydrate (66 mg, 0.4 mmol), followed by sodium borohydride (0.7 g, 18 mmol). After stirring for two hours, the mixture was quenched by the addition of water (30 mL). The mixture was extracted with EtOAc, then the combined organics were washed with 10% NH4OH (aq) then saturated NaCl (aq). The organics were dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 20% EtOAc/hexanes to afford the title compound: 1H NMR (500 MHz, CDCl3): δ 7.55 (s, 1H), 7.53 (d, J=8.5 Hz, 1H); 7.39 (t, J=8.5 Hz, 1H); 6.96 (d, J=8.0 Hz, 1H); 2.98 (s, 3H).

Workup

  1. customthe mixture was quenched by the addition of water (30 mL)
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organics were washed with 10% NH4OH (aq)
  4. dry with materialThe organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-d7c5d5b387744e86949b174b4f75264a
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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