2-Indanone → HCID 15296101, compound

HRID 1463666Notes

Reaction equation

HRID 1463666 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].Cl.[N:12]1[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[CH:14][CH:13]=1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1C=CC=CC=1>[N:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:1]2([CH2:18][C:15]3[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][C:2]2=[O:10])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 119832-IndanoneHCID 14798Sodium HydroxideHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 15296101HCID 15296101, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 241BenzeneSolvent

Procedure

To stirred mixture of 2-indanone (2.64 g, 0.02 mol), 4-picolyl chloride hydrochloride (7.22 g, 0.044 mol), and benzyltriethylammonium chloride (0.45 g, 0.002 mol) in 100 ml of benzene was added 1N sodium hydroxide (84 ml, 0.084 mol) dropwise over a period of 30 min. The mixture was stirred for an additional 2.5 h. at room temperature, then heated to 60° and maintained at this temperature for 1 h. Thin layer chromatographic analysis indicated that the reaction was complete. The reaction mixture was cooled, the organic layer was separated, and diluted with an additional 80 ml of benzene. The benzene solution was extracted with 100 ml of 1N HCl. The acidic layer was basified with 10% sodium hydroxide, wherein the crude product separated as a gum. The crude material was crystallized from cyclohexane, and further purified by recrystallization from cyclohexane to give 1,1-bis(4-pyridinylmethyl)-1,3-dihydro-2H-indene-2-one as a white solid, 0.300 g, m.p. 95°-96°. NMR (200 MHz, CDCl3) δ 2.66 (s, 2H); 3.07-3.34 (d, 4H); 6.73 (d, 4H); 6.82-7.47 (m, 4H). IR (nujol) 1714 cm-1. Analysis. Calcd. for C21H18N2O: C, 80.23; H, 5.77; N, 8.91. Found: C, 80.47; H, 5.76; N, 8.89.

Workup

  1. stirringThe mixture was stirred for an additional 2.5 h. at room temperature
  2. temperatureheated to 60°
  3. temperaturemaintained at this temperature for 1 h
  4. temperatureThe reaction mixture was cooled
  5. customthe organic layer was separated
  6. additiondiluted with an additional 80 ml of benzene
  7. extractionThe benzene solution was extracted with 100 ml of 1N HCl
  8. customseparated as a gum
  9. customThe crude material was crystallized from cyclohexane
  10. customfurther purified by recrystallization from cyclohexane

Sources & evidence

ORD record
ord-b9ced5f36b77422b800c617bcb24b679
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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