Diethyl Ether → HCID 68122540, compound

HRID 329175Notes

Reaction equation

HRID 329175 reaction equation
[Br-:1].C([O:5][C:6]1[C:15]2[N+:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Br:16])(=O)C.[CH2:17]([O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)[CH:18]=[CH2:19].CCOCC>C(O)(C)C>[CH2:17]([O:20][C:21]1[CH:27]=[CH:26][C:24]([NH3+:25])=[CH:23][CH:22]=1)[CH:18]=[CH2:19].[Br-:16].[Br:16][C:7]1[CH:8]=[CH:9][N+:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]=1[OH:5].[Br-:1]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 65042044-(allyloxy)anilineHCID 214389591-(Acetyloxy)-2-bromoquinolizin-5-ium bromide

Product 1

HCID 68122540HCID 68122540, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1-acetoxy-2-bromoquinolizinium bromide (10.0 g., 0.029 mole) in isopropanol (200 ml.) was added p-allyloxyaniline (11.0 g., 0.068 mole). The stirred mixture was boiled under reflux for 4.5 hours. The reaction mixture was cooled at room temperature overnight, and the solid was removed by filtration and washed with ether, providing 5.0 g. of product. The supernatant solution was treated with ether and refrigerated, providing another 5.0 g. of product, making the total yield 10.0 g. (77%). Recrystallization from isopropanol produced a light yellow powder melting at 125°-127°.

Workup

  1. temperatureunder reflux for 4.5 hours
  2. customthe solid was removed by filtration
  3. washwashed with ether
  4. customproviding 5.0 g
  5. customrefrigerated, providing another 5.0 g
  6. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-b2ee17ff9f3f4950b73c81972c5eb990
Source dataset
uspto-grants-1977_04
Patent number
US04020075

Reaction notes

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