Quinoline → 2,2,4-Trimethyldecahydroquinoline

HRID 1834113Notes

Reaction equation

HRID 1834113 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[CH3:11][C:12]1([CH3:23])[CH:21]=[C:20]([CH3:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1>>[CH3:11][C:12]1([CH3:23])[CH2:21][CH:20]([CH3:22])[CH:19]2[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[NH:13]1

Participants

3

Reactant 2

HCID 7047QuinolineHCID 89812,2,4-Trimethyl-1,2-dihydroquinoline

Product 1

HCID 226287862,2,4-Trimethyldecahydroquinoline

Procedure

The dimer of 2,2,4-trimethyldecahydroquinoline was prepared by hydrogenation of the timer of the unsaturated quinoline. In the process of preparing 2,2,4-trimethyl-1,2-dihydroquinoline (TMDQ) an amount of the dimer product is also formed. This TMDQ dimer can be separated out of the TMDQ and itself used to prepare substituted decahydroquinolines of the invention. 6-[4'-(2,2,4-trimethyl-1,2-dihydroquinolyl)]-2,2,4-trimethyl-1,2-dihydroquinoline was obtained by distillation and separation of the chemical from the reaction mix of a 2,2,4-trimethyl-1,2-dihydroquinoline preparation. The chemical had a boiling point of 198° C. at 1.3 mm Hg. The chemical was placed in an autoclave with hydrogen and a catalyst of rhodium at 5% by weight on charcoal. Reaction temperature was 210° C. and internal pressure was 2000 psig. After 24 hours, the reaction mix was cooled down, the catalyst filtered out, and the liquid subjected to distillation. A liquid fraction boiling at 190° C. at 1 mm Hg was collected and analyzed. The IR spectra and NMR spectra of the liquid was consistent with the desired product, 6-[4'-2,2,4-trimethyldecahydroquinolyl)]-2,2,4-trimethyldecahydroquinoline. The calculated carbon, hydrogen, nitrogen content of the C24H44N2 compound is 79.93% carbon, 12.30% hydrogen, and 7.77% nitrogen while the analyzed contents were 80.30% carbon, 12.43% hydrogen, and 7.63% nitrogen.

Workup

  1. customis also formed
  2. customThis TMDQ dimer can be separated out of the TMDQ and itself
  3. customto prepare substituted decahydroquinolines of the invention

Sources & evidence

ORD record
ord-9e45553824a943afa90bc8955912911d
Source dataset
uspto-grants-1978_01
Patent number
US04069195

Reaction notes

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