Sodium Hydroxide → HCID 19922474, compound

HRID 1463671Notes

Reaction equation

HRID 1463671 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[ClH:17].[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][Cl:25])=[CH:20][CH:19]=1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1C=CC=CC=1>[ClH:25].[ClH:17].[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:7]2([CH2:24][C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[C:6]3[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 699082-AcetylfluoreneHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 19922474HCID 19922474, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 241BenzeneSolvent

Procedure

The title compound was prepared following the procedure of Example 1 from 5.0 g (24 mmole) of 2-acetylfluorene, 10 g of 4-picolylchloride hydrochloride, 120 ml benzene, 200 mg of benzyltriethylammonium chloride, and 20 ml of 50% sodium hydroxide by reaction solution at 20° for 17 hrs. The title compound was obtained after an acid-base wash and crystallization from benzene-hexane (Magnesol®), m.p., >300°. NMR (CDCl3, 200 MHz) δ: 2.68(S,3H), 3.46(S,4H), 6.44(d,J=5.9 Hz,4H), 7.29-7.87(m,6H), 8.05(d,J=5.9 Hz,4H), 8.22(d,1H). HRMS calculated for C27H22N2O: 390.1732 Found: 390.1720.

Workup

  1. customThe title compound was prepared
  2. customby reaction solution at 20° for 17 hrs

Sources & evidence

ORD record
ord-083b84e8a76149c28d7145f01d77431b
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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