Quinoline, 1,2-dihydro-2,2,4,7-tetramethyl- → HCID 20543059, compound

HRID 2285991Notes

Reaction equation

HRID 2285991 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([CH3:13])=[CH:7][CH:8]=2)[NH:3]1.[H][H]>[Rh]>[CH3:1][C:2]1([CH3:14])[CH2:11][CH:10]([CH3:12])[CH:9]2[CH:4]([CH2:5][CH:6]([CH3:13])[CH2:7][CH2:8]2)[NH:3]1

Participants

4

Reactant 2

HCID 74551Quinoline, 1,2-dihydro-2,2,4,7-tetramethyl-HCID 178418361HCID 178418361, compound3×

Product 1

HCID 20543059HCID 20543059, compound

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

2,2,4,7-tetramethyldecahydroquinoline was prepared by reacting 125 grams of 2,2,4,7-tetramethyl-1,2-dihydroquinoline with hydrogen using 3 grams of rhodium at 5% by weight on charcoal as the catalyst and operating at 185° C., a 1000 psig pressure, for 24 hours. The desired product was confirmed by NMR spectral analysis and its carbon, hydrogen, nitrogen content (calculated contents for C13H25N is the same as above and analyzed contents were 78.95% carbon, 13.30% hydrogen, and 6.80% nitrogen). The product was 95% pure as determined by vapor pressure chromotography and boiled at about 65° C. at 1 mm of Hg.

Workup

  1. customoperating at 185° C.

Sources & evidence

ORD record
ord-7bb4279018c44b1e8d1f08ba9fe4b666
Source dataset
uspto-grants-1982_04
Patent number
US04326061

Reaction notes

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