Bromomethyl 4-methoxyphenyl ketone → HCID 10970919, compound

HRID 1421262Notes

Reaction equation

HRID 1421262 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][CH3:11])[CH:4]=1.[CH3:12][O:13][C:14]1[CH:23]=[CH:22][C:17]([C:18](=[O:21])[CH2:19][Br:20])=[CH:16][CH:15]=1>CC(C)=O>[Br-:20].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N+:6]([CH2:19][C:18]([C:17]2[CH:22]=[CH:23][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[O:21])=[C:5]([CH2:9][CH2:10][CH3:11])[CH:4]=1

Participants

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 110840544-Methoxy-2-n-propylpyridine

Product 1

HCID 10970919HCID 10970919, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-methoxy-2-n-propylpyridine (45.7 g, 0.3 mol) and 4-methoxyphenacylbromide (69.2 g, 0.3 mol) in 400 ml of dry acetone was heated to reflux for eight hours. The mixture was cooled and the precipitate was isolated and dried to afford 103.8 g (90%) of 4-methoxy-1-(4-methoxyphenacyl)-2-n-propylpyridinium bromide. The quaternary salt (103.8 g) was suspended in 480 ml of water and sodium hydrogen carbonate (102.0 g) was added. The mixture was refluxed for two hours. The resulting precipitate was filtered off, washed with water and dried to yield overall 73.2 g (86%) of 1-ethyl-7-methoxy-2-(4-methoxyphenyl)indolizine. M.p. 101-3° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.10 (t, 3H), 2.77 (q, 2H), 3.77 (s, 3H), 3.80 (s, 3H), 6.23 (dd, 1H), 6.65 (d, 1H), 7.00 (d, 2H), 7.35 (s, 1H), 7.38 (d, 2H), 8.06 (d, 1H).

Workup

  1. temperatureto reflux for eight hours
  2. temperatureThe mixture was cooled
  3. customthe precipitate was isolated
  4. customdried

Sources & evidence

ORD record
ord-d38fe1380c9c4839a06effbaee493567
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

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