Benzyltrimethylammonium hydroxide → HCID 13180342, compound

HRID 1075190Notes

Reaction equation

HRID 1075190 reaction equation
[O:1]=[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-].[CH2:19]([N+:26](C)(C)C)[C:20]1C=CC=C[CH:21]=1>C(#N)C=C>[O:1]=[C:2]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:21][CH2:20][C:19]#[N:26]

Participants

4

Reactant 2

HCID 66854Benzyltrimethylammonium hydroxideHCID 3759123-Deoxyviridicatin

Product 1

HCID 13180342HCID 13180342, compound

Reagents, catalysts & solvents 1

HCID 7855AcrylonitrileSolvent

Procedure

6.9 g of 1,2-dihydro-2-oxo-4-phenylquinoline are suspended in 45 ml of acrylonitrile, and 3 ml of benzyltrimethylammonium hydroxide are added at 40° to 45° C. During this addition, the mixture starts to boil. After boiling for ten minutes, the acrylonitrile is largely distilled off in vacuo. The residue is heated with 300 ml of ethanol to the boiling point, undissolved material is filtered off and the filtrate is treated with active charcoal and concentrated to 200 ml. The mixture is left to stand for 12 hours and the title compound which has separated out (6.4 l g of m. 162°-165° C.) is filtered off.

Workup

  1. additionDuring this addition
  2. waitAfter boiling for ten minutes
  3. distillationthe acrylonitrile is largely distilled off in vacuo
  4. temperatureThe residue is heated with 300 ml of ethanol to the boiling point, undissolved material
  5. filtrationis filtered off
  6. additionthe filtrate is treated with active charcoal
  7. concentrationconcentrated to 200 ml
  8. waitThe mixture is left
  9. customthe title compound which has separated out (6.4 l g of m. 162°-165° C.)
  10. filtrationis filtered off

Sources & evidence

ORD record
ord-a3c0343ad4114365bc9223f8f5d10a28
Source dataset
uspto-grants-1983_07
Patent number
US04395414

Reaction notes

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