Iodoethane → HCID 19607936, compound

HRID 1603091Notes

Reaction equation

HRID 1603091 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-57f829314a5441f987d8df737953988c
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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