Phosphorus oxychloride → HCID 18596278, compound

HRID 745521Notes

Reaction equation

HRID 745521 reaction equation
P(Cl)(Cl)([Cl:3])=O.[NH2:6][C:7]1[N:8]=[C:9]([Cl:24])[C:10]2[CH2:19][C@H:18]3[C@@H:13]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:20][CH2:21][CH3:22])[CH2:12][C:11]=2[N:23]=1>>[ClH:3].[NH2:6][C:7]1[N:8]=[C:9]([Cl:24])[C:10]2[CH2:19][C@H:18]3[C@@H:13]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:20][CH2:21][CH3:22])[CH2:12][C:11]=2[N:23]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18596258HCID 18596258, compound

Product 1

HCID 18596278HCID 18596278, compound

Procedure

The 4-hydroxy product thus obtained was refluxed with 4 ml. of phosphorous oxychloride. The reaction mixture, containing trans-(±)-2-amino-4-chloro-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline formed in the above reaction, was poured onto ice and the resulting aqueous mixture made basic. The basic mixture was filtered and the insoluble material dissolved in 0.1N aqueous hydrochloric acid. The hydrochloride salt thus prepared was recrystallized from ethanol to yield trans-(±)-2-amino-4-chloro-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline hydrochloride having the following physical characteristics. Mass spectrum, molecular ion at 280, smaller peak at 282.

Workup

  1. temperaturewas refluxed with 4 ml
  2. customformed in the above reaction
  3. additionwas poured onto ice
  4. filtrationThe basic mixture was filtered
  5. dissolutionthe insoluble material dissolved in 0.1N aqueous hydrochloric acid
  6. customThe hydrochloride salt thus prepared
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-e8ea720f14bc416ab5011486651be7d6
Source dataset
uspto-grants-1986_07
Patent number
US04599339

Reaction notes

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