4-Ethoxyaniline → HCID 68122063, compound

HRID 329172Notes

Reaction equation

HRID 329172 reaction equation
[Br-:1].[C:2]([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)[CH3:3].CCOC1C=CC(N)=CC=1>C(O)(C)C>[CH3:3][CH2:2][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH3+:10])=[CH:14][CH:15]=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

4

Reactant 2

HCID 90764-EthoxyanilineHCID 214389591-(Acetyloxy)-2-bromoquinolizin-5-ium bromide

Product 1

HCID 68122063HCID 68122063, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1-acetoxy-2-bromoquinolizinium bromide (30.0 g., 0.09 mole) in isopropanol (600 ml.) was added p-phenetidin (24.0 g., 0.18 mole). The stirred mixture was boiled under reflux for 4 hours, during which time solid had precipitated from solution. The cooled mixture was filtered and washed with ether. The product as yellow needles weighed 37.0 g. (97%). Recrystallization from alcohol-ether provided yellow needles which melted at 161°-162°.

Workup

  1. temperatureunder reflux for 4 hours, during which time solid
  2. customhad precipitated from solution
  3. filtrationThe cooled mixture was filtered
  4. washwashed with ether
  5. customRecrystallization from alcohol-ether provided yellow needles which melted at 161°-162°

Sources & evidence

ORD record
ord-9ba1460eb2a54db78aef030d450e98ce
Source dataset
uspto-grants-1977_04
Patent number
US04020075

Reaction notes

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