Phosphinic Acid → HCID 21109913, compound

HRID 1766177Notes

Reaction equation

HRID 1766177 reaction equation
N[C:2]1[C:7]([Br:8])=[CH:6][C:5]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[Br:16].N([O-])=O.[Na+].[PH2](O)=O>S(=O)(=O)(O)O.O>[Br:8][C:7]1[CH:6]=[C:5]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:4]=[C:3]([Br:16])[CH:2]=1

Participants

6

Reactant 3

HCID 4124402Phosphinic AcidHCID 11175554HCID 11175554, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21109913HCID 21109913, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-2.5 °C

Procedure

A solution of 3.5 g (0.01 mol) of 4-(4-amino-3,5-dibromophenyl)-4-oxobutanoic acid in 50 ml of 1N aqueous sulphuric acid was treated dropwise with a solution of 0.76 g (0.011 mol) of sodium nitrite in 10 ml of water while maintaining a reaction temperature of −5 to 0° C. The mixture was stirred for a further 30 minutes at a temperature of 0° C., then 50 ml of hypo-phosphorous acid were added dropwise while maintaining the same temperature and stirred for another 1 hour at a temperature of 0° C. The mixture was decolorised and a colourless crystalline substance was precipitated. The mixture was diluted with 100 ml of water, the precipitate formed was suction filtered, washed thoroughly with water and then dried in a circulating air dryer. 3.1 g (92% of theoretical) of colourless crystals were obtained, m.p. 137–138° C.

Workup

  1. temperaturewhile maintaining the same temperature
  2. stirringstirred for another 1 hour at a temperature of 0° C
  3. customa colourless crystalline substance was precipitated
  4. additionThe mixture was diluted with 100 ml of water
  5. customthe precipitate formed
  6. filtrationfiltered
  7. washwashed thoroughly with water
  8. customdried in a circulating air dryer
  9. custom3.1 g (92% of theoretical) of colourless crystals were obtained

Sources & evidence

ORD record
ord-d11fab0466644a0b811ce9557faf19b2
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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