Isopropyl iodide → HCID 20490770, compound

HRID 435073Notes

Reaction equation

HRID 435073 reaction equation
[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH3:12])=[CH:7][CH:8]=2)[NH:3]1.C(=O)([O-])[O-].[K+].[K+].I[CH:20]([CH3:22])[CH3:21].ICCC>O>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH3:12])=[CH:7][CH:8]=2)[N:3]1[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 20428348Quinoline, 1,2,3,4-tetrahydro-2,7-dimethyl-

Product 1

HCID 20490770HCID 20490770, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,7-dimethyl-1,2,3,4-tetrahydroquinoline (32.2 g, 0.2 m), potassium carbonate (15.0 g, 0.11 m), and 2-iodopropane (51 g, 0.3 m) was heated at 90°-95° C. for 5.5 hr. Progress of the reaction was slow. An additional quantity (34.0 g) of iodopropane was added and the mixture refluxed for 24 hrs. longer. Starting material was still evident by thin-layer chromatography. The reaction mixture was drowned into 200 ml water and extracted with chloroform (50 ml). The organic layer was treated with 10 ml of acetic anhydride for 1 hr. at 90°-95° C. to convert the 2,7-dimethyl-1,2,3,4-tetrahydroquinoline into N-acetyl-2,7-dimethyl-1,2,3,4-tetrahydroquinoline, which enables the recovery of the pure product by distillation. The organic layer was distilled under vacuum to give 23.4 g (55% yield) of product which boiled at 85° C. at 0.21.1 mm Hg.

Workup

  1. temperaturewas heated at 90°-95° C. for 5.5 hr
  2. temperaturethe mixture refluxed for 24 hrs
  3. extractionextracted with chloroform (50 ml)
  4. additionThe organic layer was treated with 10 ml of acetic anhydride for 1 hr
  5. customat 90°-95° C.
  6. distillationby distillation
  7. distillationThe organic layer was distilled under vacuum

Sources & evidence

ORD record
ord-93fe7a038fd24d68955619ae95095969
Source dataset
uspto-grants-1983_08
Patent number
US04400318

Reaction notes

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