Isopropanol → HCID 68121657, compound

HRID 329173Notes

Reaction equation

HRID 329173 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)C.COC1C=CC(N)=CC=1.C(O)(C)C>C(OCC)(=O)C>[CH3:2][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

5

Reactant 3

HCID 3776IsopropanolHCID 7732P-AnisidineHCID 214389591-(Acetyloxy)-2-bromoquinolizin-5-ium bromide

Product 1

HCID 68121657HCID 68121657, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a 500 ml., 3-neck flask was placed a mixture of 1-acetoxy-2-bromoquinolizinium bromide (12.0 g., 0.035 mole), p-anisidine (9.6 g., 0.078 mole) and isopropanol (240 ml.). The stirred solution was boiled under reflux for 4.5 hours. After cooling in an ice bath the reaction mixture was treated with ethyl acetate to induce crystallization. The yellow solid (11.0 g., 74%) was removed by filtration, washed with ether and ethyl acetate and dried at 63°. Recrystallization from isopropanol/ethyl actate provided a pale yellow powder which melted at 129°-133°.

Workup

  1. custom, 3-neck flask was placed
  2. temperatureunder reflux for 4.5 hours
  3. temperatureAfter cooling in an ice bath the reaction mixture
  4. customcrystallization
  5. customThe yellow solid (11.0 g., 74%) was removed by filtration
  6. washwashed with ether and ethyl acetate
  7. customdried at 63°
  8. customRecrystallization from isopropanol/ethyl actate
  9. customprovided a pale yellow powder which melted at 129°-133°

Sources & evidence

ORD record
ord-74a3673a5db9462587cefd993c61b061
Source dataset
uspto-grants-1977_04
Patent number
US04020075

Reaction notes

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