Water → HCID 14552443, compound

HRID 654742Notes

Reaction equation

HRID 654742 reaction equation
N[C:2]1[S:3][C:4]2[CH2:13][C@H:12]3[C@@H:7]([CH:8]=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][N:11]3[CH2:14][CH2:15][CH3:16])[CH2:6][C:5]=2[N:22]=1.N([O-])=O.[Na+].O.[PH2](O)=O>P(=O)(O)(O)O>[CH2:14]([N:11]1[C@@H:12]2[C@H:7]([CH2:6][C:5]3[N:22]=[CH:2][S:3][C:4]=3[CH2:13]2)[CH:8]=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10]1)[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962Water2×HCID 4124402Phosphinic AcidHCID 18632325HCID 18632325, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14552443HCID 14552443, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

A solution of 0.5 g (1.5 mmole) of ethyl 2-amino-5-propyl-trans-4,4a,5,6,8a,9-hexahydrothiazolo-[4,5-g]quinoline-7-carboxylate (Example 3) in 50 ml of 85% phosphoric acid was cooled to 0° C. Then 110 mg (1.8 mmole) of sodium nitrite dissolved in as small an amount of water as possible was slowly adeed under the surface of the reaction mixture. The resulting mixture was added dropwise to 50 ml of 50% hypophosphorous acid (H3PO2) at 0° C. The mixture was stirred at room temperature until gas evolution ceased. This took about 1 hour. The mixture was poured onto ice, and the hydrogen ion concentration of the mixture was adjusted to pH 11. Water was added to dissolve the preoipitate that formed; then the product was extracted into a solution of CHCl3 /i-PrOH (3:1). This solution was dried using sodium sulfate and evaporated to give 0.46 g of the title product.

Workup

  1. customThis took about 1 hour
  2. additionThe mixture was poured onto ice
  3. dissolutionto dissolve the preoipitate
  4. customthat formed
  5. extractionthen the product was extracted into a solution of CHCl3 /i-PrOH (3:1)
  6. customThis solution was dried
  7. customevaporated

Sources & evidence

ORD record
ord-1945b9d9c1974866b575351e78f5885b
Source dataset
uspto-grants-1992_07
Patent number
US05134143

Reaction notes

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