Ammonia → HCID 20394545, compound

HRID 261612Notes

Reaction equation

HRID 261612 reaction equation
C[CH:2]1[C:11]2[C:10]3[CH:12]=[CH:13][CH2:14][CH2:15][C:9]=3[CH:8]=[CH:7][C:6]=2[NH:5][CH2:4][CH2:3]1.N.[Li].[CH2:18](O)C>CCOCC.O>[CH3:18][N:5]1[CH:6]2[CH:11]([C:10]3[CH2:12][CH:13]=[CH:14][CH2:15][C:9]=3[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 702EthanolHCID 3028194LithiumHCID 20394548HCID 20394548, compound

Product 1

HCID 20394545HCID 20394545, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

1-Methyl-1,2,3,4,7,8-hexahydrobenzo[f]-quinoline is dissolved in 200 ml of ether and added to 1.5 l of liquid ammonia. Lithium ribbon (16 g) is added portionwise over a period of 15 minutes. After stirring a few minutes, absolute ethanol is added dropwise until the color is discharged (500 ml added over a period of 2.5 hours). More ether is added and the ammonia is boiled off. While cooling in an ice bath, the mixture is diluted to about 1500 ml with water. The layers are separated and the aqueous layer is reextracted with ether. The combined organic layers are dried over potassium carbonate, filtered and the solvent is removed in vacuo leaving the title compound as a crude product.

Workup

  1. additionadded over a period of 2.5 hours)
  2. temperatureWhile cooling in an ice bath
  3. customThe layers are separated
  4. dry with materialThe combined organic layers are dried over potassium carbonate
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-1ba6f8d1fb874e9b8f5a10b9e760f048
Source dataset
uspto-grants-1979_08
Patent number
US04166183

Reaction notes

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