Triethylamine → HCID 21498215, compound

HRID 1730494Notes

Reaction equation

HRID 1730494 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[NH:12][NH2:13].[C:14](Cl)(=O)[CH2:15][CH2:16][CH3:17].C(N(CC)CC)C>ClCCl>[CH2:15]([C:14]1[N:6]2[CH:5]=[CH:4][C:3]3[C:8]([C:7]2=[N:12][N:13]=1)=[CH:9][CH:10]=[CH:11][C:2]=3[Br:1])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 21498249HCID 21498249, compound

Product 1

HCID 21498215HCID 21498215, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-1-hydrazinoisoquinoline (4.76 g., 0.02 mol.) and butyryl chloride (2.1 ml., 0.02 mol.) in dichloromethane (100 ml.) was allowed to reflux overnight. The solvent was removed in vacuo and the residue was heated at reflux for three hours in xylene (100 ml.) and triethylamine (2.8 ml., 0.02 mol.). The mixture was filtered and the xylene removed in vacuo to provide the crude product. Recrystallization from ethanol (≈100 ml.) gave the pure product, 4.4 g. (76%); m.p. 197°-199°C., m.p. (hydrochloride salt) 200°-201°C.

Workup

  1. temperatureto reflux overnight
  2. customThe solvent was removed in vacuo
  3. temperaturethe residue was heated
  4. temperatureat reflux for three hours in xylene (100 ml.)
  5. filtrationThe mixture was filtered
  6. customthe xylene removed in vacuo

Sources & evidence

ORD record
ord-3121f400307e476593b59adc2a29bfb1
Source dataset
uspto-grants-1976_11
Patent number
US03992539

Reaction notes

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