Sodium Hydroxide → HCID 19075055, compound

HRID 965006Notes

Reaction equation

HRID 965006 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][N:15](C(OC)=O)[CH2:14][CH2:13]3)=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH-].[Na+].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25]>CO>[N:12]1([C:8]2[CH:7]=[C:6]3[C:11]([C:2](=[S:25])[CH:3]=[CH:4][NH:5]3)=[CH:10][CH:9]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 178501935HCID 178501935, compound

Product 1

HCID 19075055HCID 19075055, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxy-7-(4-methoxycarbonyl-1-piperazinyl)quinoline (0.32 g, 1.1 mmol) dissolved in methanol (5 ml) was added with 2N sodium hydroxide (1.6 ml) and stirred with heating for 12 hours. After allowing to cool, methanol was removed under reduced pressure. The residue was added with water (10 ml) and adjusted by 5% hydrochloric acid to pH 7 and the water was removed under reduced pressure. This residue was siispended in pyridine (5 ml), added with phosphorus pentasulfide (0.25 g, 1.1 mmol) and stirred at 100° C. for 1.5 hours. After allowing to cool, pyridine was removed under reduced pressure and the residue was purified by preparative TLC (Merck Art. 13895, methylene chloride : methanol : ammonia water=50 : 10 : 1) to obtain 21 mg (8%) of the titled compound.

Workup

  1. temperaturewith heating for 12 hours
  2. temperatureto cool
  3. custommethanol was removed under reduced pressure
  4. additionThe residue was added with water (10 ml)
  5. customthe water was removed under reduced pressure
  6. stirringstirred at 100° C. for 1.5 hours
  7. temperatureto cool
  8. custompyridine was removed under reduced pressure
  9. customthe residue was purified by preparative TLC (Merck Art. 13895, methylene chloride : methanol : ammonia water=50 : 10 : 1)

Sources & evidence

ORD record
ord-7cc32da3fea3451fb0dc1693203f693d
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

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