Magnesium → HCID 18475731, compound

HRID 2187468Notes

Reaction equation

HRID 2187468 reaction equation
[C:1]([C:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=1)#[N:2].[Mg]>CO>[NH3:2].[C:1]([CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([N:13]3[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]3)[CH:7]=[CH:8][CH:9]=2)[CH2:4]1)#[N:2]

Participants

5

Reactant 2

HCID 5462224MagnesiumHCID 18475776HCID 18475776, compound

Product 2

HCID 222AmmoniaHCID 18475731HCID 18475731, compoundYield 139.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Cyano-3,4-dihydro-8-[4-methyl(piperazin-1-yl)]-naphthalene (230 mg, 0.90 mmol) was dissolved in dry methanol (15 mL) and cooled to 0° C. Magnesium turnings (440 mg, 18 mmol) were added and the reaction mixture was stirred for 45 min at 0° C. and for 4 h at room temperature. The solvent was evaporated and 2 M hydrochloric acid (20 mL) was added to the residue. The mixture was stirred for 1 h, cooled on ice-bath and alkalized to pH 10 with 2 M ammonia. The solution was extracted with ethyl acetate (60+2×30 mL) and the organic phase was washed with brine (15 mL). Drying (MgSO4) and evaporation of the solvent gave 210 mg of a crude product. Purification by preparative TLC on silica using chloroform/methanol/conc. NH3 (95:5:0.5) afforded 160 mg (71% yield) of the title compound as a white solid: mp 111-112° C.; EIMS (70 eV) m/z (relative intensity) 255 (34, M+).

Workup

  1. customThe solvent was evaporated
  2. addition2 M hydrochloric acid (20 mL) was added to the residue
  3. stirringThe mixture was stirred for 1 h
  4. temperaturecooled on ice-bath
  5. extractionThe solution was extracted with ethyl acetate (60+2×30 mL)
  6. washthe organic phase was washed with brine (15 mL)
  7. customDrying
  8. custom(MgSO4) and evaporation of the solvent
  9. customgave 210 mg of a crude product
  10. customPurification by preparative TLC on silica

Sources & evidence

ORD record
ord-f05d753aa0dd40d5833529d2eb4d1a2a
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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