Diethyl Ether → HCID 68122009, compound

HRID 329174Notes

Reaction equation

HRID 329174 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.[O:17]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCOCC>C(O)(C)C>[O:17]([C:24]1[CH:25]=[CH:26][C:27]([NH3+:28])=[CH:29][CH:30]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1.[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 8764(4-Aminophenoxy)benzeneHCID 214389591-(Acetyloxy)-2-bromoquinolizin-5-ium bromide

Product 1

HCID 68122009HCID 68122009, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1-acetoxy-2-bromoquinolizinium bromide (12.0 g., 0.035 mole) in isopropanol (250 ml.) was added p-phenoxyaniline (15.0 g., 0.08 mole). The stirred mixture was boiled under reflux for 3.5 hours. The reaction mixture was treated with ether and scratched, and the precipitate was removed by filtration and dried at 63°. The mustard-yellow product weighed 11.0 g. (65%). Recrystallization from isopropanol/ether provided gold crystals melting at 123°-125°.

Workup

  1. temperatureunder reflux for 3.5 hours
  2. customthe precipitate was removed by filtration
  3. customdried at 63°
  4. customRecrystallization from isopropanol/ether

Sources & evidence

ORD record
ord-fbbce98545b34a76ac00b3d3e6376b88
Source dataset
uspto-grants-1977_04
Patent number
US04020075

Reaction notes

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