2-Methyl-1,2,3,4-tetrahydroquinoline → Hexadecane

HRID 649272

Reaction equation

HRID 649272 reaction equation
[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)N1.CC1C=C[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2N=1.CC1CCC2C(CCCC2)N1>>[CH3:17][CH2:16][CH2:15][CH2:20][CH2:19][CH2:18][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:9][CH2:10][CH2:11][CH2:2][CH3:1]

Participants

4

Reactant 3

HCID 962892-Methyl-1,2,3,4-tetrahydroquinolineHCID 5240162-Methyldecahydroquinoline (mixture of isomers)HCID 122294205,6,7,8-Tetrahydro-2-methylquinoline

Product 1

HCID 11006Hexadecane

Procedure

The autoclave was cooled and the contents were suction filtered. Gas liquid chromatographic analysis of the colorless liquid filtrate on a 6'×1/8" 10% Carbowax 20M column at 200° C. showed that the only product of the reaction was 2-methyl-1,2,3,4-tetrahydroquinoline (96% 2-methyl-1,2,3,4-tetrahydroquinoline and 4% starting material). There were no detectable amounts of 2-methyl-5,6,7,8-tetrahydroquinoline and 2-methyldecahydroquinoline. Gas liquid chromatographic analysis with an external standard showed that the absolute yield of product based on consumed starting material was 100%. The use of cyclohexane as the solvent instead of n-hexadecane gave the same result (97% of 2-methyl-1,2,3,4-tetrahydroquinoline and 3% of 2-methylquinoline).

Workup

  1. temperatureThe autoclave was cooled
  2. customat 200° C.
  3. customon consumed

Sources & evidence

ORD record
ord-cef0c9a723fd45e4bfb81215512938fa
Source dataset
uspto-grants-1988_04
Patent number
US04739063

Linked notes

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