Triethylamine → HCID 19102710, compound

HRID 1198508Notes

Reaction equation

HRID 1198508 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[NH:14][C:13]4[CH2:15][CH2:16][NH:17][CH2:18][C:12]=4[C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)#[N:27]>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[NH:14][C:13]4[CH2:15][CH2:16][N:17]([C:32](=[O:33])[C:31]5[CH:35]=[CH:36][C:28]([C:26]#[N:27])=[CH:29][CH:30]=5)[CH2:18][C:12]=4[C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 14069786HCID 14069786, compound

Product 1

HCID 19102710HCID 19102710, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.40 g (1.55 mmol) of 3-chloro-8,9,10,11-tetrahydro-7H-pyrido[3',4':4,5]pyrrolo[3,2-c]quinoline, 0.188 g (1.86 mmol) of triethylamine and 15 ml of tetrahydrofuran at 0° C. is added 0.275 g (1.55 mmol) of 4-cyanobenzoyl chloride dropwise and the reaction mixture is allowed to stir overnight while slowly reaching room temperature. A precipitate is formed overnight which is collected by filtration, washed with water and ether and dried to yield a crude product which is triturated with methanol/chloroform to yield 0.14 g (23%) of the title compound as a white solid: m.p.>300° C.; m/e 386.

Workup

  1. customwhile slowly reaching room temperature
  2. customA precipitate is formed overnight which
  3. filtrationis collected by filtration
  4. washwashed with water and ether
  5. customdried
  6. customto yield a crude product which
  7. customis triturated with methanol/chloroform

Sources & evidence

ORD record
ord-d19202aa73eb4903b340456fd9832617
Source dataset
uspto-grants-1994_01
Patent number
US05281608

Reaction notes

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