Hydrochloric Acid → 94512-47-7

HRID 1197310Notes

Reaction equation

HRID 1197310 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:9]([O-])=O.[Na+].[CH2:13]1[C:18](=[O:19])[O:17][CH2:16][C:14]1=[O:15].O.O.O.C([O-])(=O)C.[Na+]>O>[C:3]1([N:2]=[N:9][C:13]2[C:18](=[O:19])[O:17][CH2:16][C:14]=2[OH:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 521261Tetronic acidHCID 23665404Sodium Acetate TrihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 13540769894512-47-7

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

300 ml of 6N hydrochloric acid solution was placed in a 1.5-liter flask equipped with a 250-ml dropping funnel, a mechanical stirrer and a thermometer. 57.6 g (0.61 mol) of distilled aniline was added with ice cooling. A solution of 43.92 g (0.64 mol) of sodium nitrite in 90 ml of ice water was added dropwise to the resulting suspension and stirred for 40 min. The resultant diazonium salt solution was added dropwise to a solution of 60 g (0.6 mol) of tetronic acid and 120 g (0.88 mol) of sodium acetate trihydrate in 900 ml of water for 30 min. After this addition a yellow solid immediately precipitated. The reaction mixture was stirred at 10° C. for 1.5 hours, and filtered off; and the product was washed with 500 ml of cold methanol. It was dried at 35° C. in a vacuum. Concerning the product:

Workup

  1. customequipped with a 250-ml
  2. additionAfter this addition a yellow solid
  3. customimmediately precipitated
  4. stirringThe reaction mixture was stirred at 10° C. for 1.5 hours
  5. filtrationfiltered off
  6. washand the product was washed with 500 ml of cold methanol
  7. customIt was dried at 35° C. in a vacuum

Sources & evidence

ORD record
ord-40c93b902df14c2bb123106acb9e4697
Source dataset
uspto-grants-1992_05
Patent number
US05117003

Reaction notes

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