Phosphorus oxychloride → HCID 18596278, compound

HRID 1247916Notes

Reaction equation

HRID 1247916 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-d53d5846af70420987becebde0ef4452
Source dataset
uspto-grants-1985_06
Patent number
US04521421

Reaction notes

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