Hydrochloric Acid → HCID 20258989, compound

HRID 1583601Notes

Reaction equation

HRID 1583601 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([F:18])=[CH:16][C:15](N)=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([CH3:20])=[N:13]3)[CH2:4][CH2:3]1.Cl.N([O-])=O.[Na+].[PH2](O)=O.[OH-].[Na+]>C(O)CCCCCCC.O>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([F:18])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([CH3:20])=[N:13]3)[CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 20258972HCID 20258972, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20258989HCID 20258989, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 9571-OctanolCatalystHCID 962WaterSolvent2×

Procedure

To 1.5 g of 5-(4-hydroxy-1-piperidyl)-6-fluoro-8-amino-quinaldine were added 10 ml of concentrated hydrochloric acid and 3 ml of water, and 2 ml of an aqueous solution of 0.39 g of sodium nitrite was added dropwise to the mixture at -2° C. After 3 minutes one drop of n-octanol (defoaming agent) was added to the mixture. Then, 5.7 g of hypophosphorous acid (50% aqueous solution) already cooled to 0° C. was added dropwise to the mixture at -2° C. Thereafter, stirring was continued at 0°-5° C. for 7 hours. The reaction mixture was poured into water, rendered alkaline with an aqueous sodium hydroxide solution and extracted with dichloromethane. The extract was dried over sodium sulfate and the solvent was distilled off to give 0.68 g of 5-(4-hydroxy-1-piperidyl)-6-fluoroquinaldine.

Workup

  1. additionwas added dropwise to the mixture at -2° C
  2. additionwas added dropwise to the mixture at -2° C
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract was dried over sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-408b3cfc1cf343c8889bf329bc5c3625
Source dataset
uspto-grants-1985_11
Patent number
US04552879

Reaction notes

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