Iodoethane → HCID 19607936, compound

HRID 745051Notes

Reaction equation

HRID 745051 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5]([NH:7][C:8]1[CH:25]=[CH:24][C:11]([C:12]([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)=[O:13])=[CH:10][CH:9]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:35](I)[CH3:36]>CC(C)=O>[CH2:35]([O:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5]([NH:7][C:8]1[CH:25]=[CH:24][C:11]([C:12]([N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)=[O:13])=[CH:10][CH:9]=1)=[O:6])[CH3:36]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 19607913HCID 19607913, compound

Product 1

HCID 19607936HCID 19607936, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-[4-(3-hydroxybenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.4 g) in acetone (5 ml) are added potassium carbonate (0.22 g) and ethyl iodide (0.34 g), and the mixture is refluxed for 5 hours. Then, acetone is distilled off under reduced pressure and water is added to the residue. The precipitated crystal is collected by filtration, and recrystallized from methanol to give 1-[4-(3-ethoxybenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (0.36 g) as white powder, m.p. 170.5°-171.5° C.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. distillationThen, acetone is distilled off under reduced pressure and water
  3. additionis added to the residue
  4. filtrationThe precipitated crystal is collected by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e270c3d909ea4da8a3072e45ab95fd11
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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