Hydrogen Bromide → HCID 18599046, compound

HRID 485672Notes

Reaction equation

HRID 485672 reaction equation
[CH2:1]([N:4]1[C@H:13]2[C@@H:8]([CH2:9][C:10](=O)[CH2:11][CH2:12]2)[CH2:7][CH2:6][CH2:5]1)[CH2:2][CH3:3].[BrH:15].BrBr.[NH2:18][C:19]([NH2:21])=[S:20]>C(O)(=O)C.C(O)C>[BrH:15].[BrH:15].[NH2:21][C:19]1[S:20][C:11]2[CH2:12][C@H:13]3[C@@H:8]([CH2:7][CH2:6][CH2:5][N:4]3[CH2:1][CH2:2][CH3:3])[CH2:9][C:10]=2[N:18]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 2723790ThioureaHCID 13457872(8aR-trans)-octahydro-1-propyl-6(2H)-quinolinone

Product 1

HCID 18599046HCID 18599046, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Five grams of trans-(±)-1-n-propyl-6-oxodecahydroquinoline were dissolved in 30 ml. of glacial acetic acid. Five and eight tenths milliliters of 37% by weight hydrogen bromide in glacial acetic acid were added followed by the dropwise additions of 1.5 ml. of bromine dissolved in glacial acetic acid. The reaction mixture was illuminated with ultraviolet radiation using a commercially available sunlamp. The illuminated reaction mixture was stirred for one-half hour after all the reactants had been added. Volatile constituents were removed from the reaction mixture in vacuo yielding, as a residue, trans-(±)-1-n-propyl-6-oxo-7-bromodecahydroquinoline hydrobromide. One hundredth mole of this salt was dissolved in 50 ml. of ethanol. Eighty-four hundredths grams of thiourea were added thereto. The resulting mixture was refluxed for about 18 hours under a nitrogen blanket. A colorless solid began to form after about 20 minutes. The reaction mixture was cooled to about 0° C. and the solid, which had continued to form, was separated by filtration. The filter cake was dried in vacuo. One and fifteen hundredths grams of trans-(±)-2-amino-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline dihydrobromide salt were obtained. The salt melted above 255° C., tlc (9:1 chloroform:methanol plus a trace of ammonium hydroxide) Rf =0.13.

Workup

  1. customThe reaction mixture was illuminated with ultraviolet radiation
  2. customThe illuminated reaction mixture
  3. additionhad been added
  4. customVolatile constituents were removed from the reaction mixture in vacuo
  5. customyielding, as a residue
  6. dissolutionOne hundredth mole of this salt was dissolved in 50 ml
  7. temperatureThe resulting mixture was refluxed for about 18 hours under a nitrogen blanket
  8. customto form after about 20 minutes
  9. customto form
  10. customwas separated by filtration
  11. customThe filter cake was dried in vacuo

Sources & evidence

ORD record
ord-1ca5c93206ba40b984196a7708e0813f
Source dataset
uspto-grants-1985_08
Patent number
US04537893

Reaction notes

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