Hydrochloric Acid → HCID 178456238, compound

HRID 2164870Notes

Reaction equation

HRID 2164870 reaction equation
CSC1N=CC2C[C@H]3[C@@H](CCCN3CCC)CC=2N=1.Cl.Cl.Cl.[OH:23][C:24]1[N:25]=[CH:26][C:27]2[CH2:36][C@H:35]3[C@@H:30]([CH2:31][CH2:32][CH2:33][N:34]3[CH2:37][CH2:38][CH3:39])[CH2:29][C:28]=2[N:40]=1.CO>C(OCC)(=O)C.C(O)C>[OH:23][C:24]1[N:25]=[CH:26][C:27]2[CH2:36][C@H:35]3[C@@H:30]([CH2:31][CH2:32][CH2:33][N:34]3[CH2:37][CH2:38][CH3:39])[CH2:29][C:28]=2[N:40]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 18596516HCID 18596516, compoundHCID 178456239HCID 178456239, compound

Product 1

HCID 178456238HCID 178456238, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.93 g. of trans-(±)-2-methylthio-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline and 2 ml. of 12N aqueous hydrochloric acid was heated to reflux temperature for 1.5 hours. The reaction mixture was then concentrated in vacuo. Methanol was added and the reaction mixture again concentrated in vacuo. A residual green oil, comprising trans-(±)-2-hydroxy-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline dihydrochloride formed in the above reaction was dissolved in a mixture of ethyl acetate and ethanol. As the green oil dissolved, crystals formed. Trans-(±)-2-hydroxy-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline dihydrochloride thus prepared had the following physical characteristics: Rf (methanol)=0.5; molecular ion at 247; yield=0.62 g.

Workup

  1. additionA mixture of 0.93 g
  2. temperatureto reflux temperature for 1.5 hours
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. additionMethanol was added
  5. concentrationthe reaction mixture again concentrated in vacuo
  6. customformed in the above reaction
  7. dissolutionAs the green oil dissolved
  8. customcrystals formed

Sources & evidence

ORD record
ord-2cd00f0f4650440d8c35178b4f2bbdb6
Source dataset
uspto-grants-1985_03
Patent number
US04507478

Reaction notes

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