Hydrochloric Acid → 2-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

HRID 489288Notes

Reaction equation

HRID 489288 reaction equation
[O:1]=[C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:14])[CH2:7][CH2:8][CH2:9]2)=[CH:4][NH:3]1.I[CH2:16][CH2:17][CH2:18][CH3:19].[H-].[Na+].Cl>CN(C=O)C>[CH2:16]([N:3]1[C:2](=[O:1])[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:14])[CH2:7][CH2:8][CH2:9]2)=[CH:4]1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 222665143,8-Dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

Product 1

HCID 222664802-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,8-Dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-010) (770 mg, 4.1 mmol) was dissolved in DMF (15 mL) and to the reaction mixture was added 1-iodobutane (0.51 mL, 4.5 mmol) and sodium hydride (60% oil suspension, 180 mg, 4.5 mmol), and the reaction mixture was stirred at room temperature for 3 h. To the reaction mixture was added dilute hydrochloric acid (1 mol/L, 60 mL) and the reaction mixture was extracted with ethyl acetate (150 mL), washed with brine (50 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (toluene/ethyl acetate) to give 2-butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-011) (610 mg, 61%) as a white crystal.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (150 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1094d7d993cc4f51919f32f338a979b2
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

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