Sodium Hydroxide → HCID 19922433, compound

HRID 1463667Notes

Reaction equation

HRID 1463667 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].Cl.[N:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1C=CC=CC=1>[N:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:1]2([CH2:19][C:16]3[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=3)[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][C:2]2=[O:11])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 682662-TetraloneHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 19922433HCID 19922433, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 241BenzeneSolvent2×

Procedure

To a stirred mixture of 2-tetralone (4.4 g, 0.03 mol), 4-picolylchloride hydrochloride (10.82 g, 0.066 mol), and benzyltriethylammonium chloride (1.4 g, 0.006 mol) in 80 ml of benzene was added 1N sodium hydroxide (178 ml, 0.178 mol) dropwise during a period of 1 h. at room temperature. Stirring was continued for another hour. Additional benzene (80 ml) was added, the organic layer was separated, and dried over sodium sulfate. The inorganic salts were filtered off, and to the filtrate was added 5 g of Florisil/(a magnesium silicate adsorbent). The mixture was stirred for 30 min., the solids were filtered off, and the benzene was removed by rotary evaporation. The oily residue was dissolved in the minimum amount of ethanolic HCl (5 ml), and a small amount of acetone was added, whereupon the dihydrochloride salt crystallized out of solution. This salt was collected (1.57 g), redissolved in water, and made basic with potassium carbonate. The solids obtained were air dried (900 mg), and recrystallized from cyclohexane to give 1,1-bis(4-pyridinylmethyl)-2(1H)-naphthalenone as a white solid, 460 mg, m.p. 111°-112°. NMR (200 MHz, CDCl3) δ 1.9 (m, 4H); 3.30 (d, 4H); 6.55 (d, 4H); 6.95 (d, 1H); 7.15 (t, 1H); 7.45 (t, 1H); 7.66 (d, 1H); 8.30 (d, 4H). IR (nujol) 1709 cm-1. Analysis. Calcd. for C22H20N2O: C, 80.46; H, 6.14; N, 8.53. Found: C, 80.12; H, 6.25; N, 8.61.

Workup

  1. waitwas continued for another hour
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationThe inorganic salts were filtered off
  5. additionto the filtrate was added 5 g of Florisil/(a magnesium silicate adsorbent)
  6. stirringThe mixture was stirred for 30 min.
  7. filtrationthe solids were filtered off
  8. customthe benzene was removed by rotary evaporation
  9. dissolutionThe oily residue was dissolved in the minimum amount of ethanolic HCl (5 ml)
  10. additiona small amount of acetone was added, whereupon the dihydrochloride salt
  11. customcrystallized out of solution
  12. customThis salt was collected (1.57 g)
  13. dissolutionredissolved in water
  14. customThe solids obtained
  15. customdried (900 mg)
  16. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-f845c6841512426089542f6d2185c066
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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