Hydrochloric Acid → HCID 87421083, compound

HRID 1920894Notes

Reaction equation

HRID 1920894 reaction equation
[C:1]1([P:7]([CH2:15][CH:16]=O)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:19][OH:20].[OH-].[Na+].Cl>C(O)C.O>[C:1]1([P:7]([CH2:15]/[CH:16]=[N:19]\[OH:20])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 11042963(Diphenyl-phosphinoyl)-acetaldehyde

Product 1

HCID 87421083HCID 87421083, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of (diphenyl-phosphinoyl)-acetaldehyde example 1d (2.4 g, 9.0 mmol) and hydroxylamine hydrochloride (0.68 g, 10.0 mmol) in ethanol (50 mL) and water (100 mL) was added at 0° C. an aqueous solution of sodium hydroxide (50%, 5 mL) added dropwise within a 10 min period. After stirring at room temperature overnight, the resulting mixture was acidified with HCl (4 N). The mixture was then extracted with dichloromethane and the combined organic layers were then washed with water and brine and then dried over sodium sulfate, filtered and evaporated to afford the title compound (3.75 g, 98%) which was obtained as a light yellow solid. MS m/e (EI): 260.0 [M].

Workup

  1. additionadded dropwise within a 10 min period
  2. extractionThe mixture was then extracted with dichloromethane
  3. washthe combined organic layers were then washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4918ede28e5944abad1ce9e499836eee
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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