Hydrochloric Acid → HCID 69896393, compound

HRID 353450Notes

Reaction equation

HRID 353450 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[N:10]([O-])=O.[Na+].[O:14]=[C:15]1[O:21][C@H]([C@H](CO)O)C(O)=[C:16]1[OH:17]>O>[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[N:5]([C:16](=[O:17])[C:15]([OH:21])=[O:14])[NH2:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72402-ChloroanilineHCID 23668193Sodium NitriteHCID 54670067L-Ascorbic Acid

Product 1

HCID 69896393HCID 69896393, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-1 °C

Procedure

To a 500 ml flask under a nitrogen atmosphere, concentrated HCl (80 ml, 32%, 0.81 moles) was charged and cooled to −2 to 0° C. 2-Chloroaniline (16 ml, 19.4 g, 0.15 moles) was added dropwise at −2 to 0° C. Sodium nitrite (12.4 g, 0.18 moles) dissolved in water (25 ml) was added dropwise to the acidic mixture through an addition funnel over a period of 30 minutes at −2 to 0° C. The resulting mixture was stirred for 1 hour at −2 to 0° C. L-Ascorbic acid (26.6 g, 0.15 moles) dissolved in water (130 ml) was added through an addition funnel over a period of 1 hour at −2 to 0° C. The reaction was allowed to come to room temperature (18-20° C.) over a period of 30 minutes, then heated to 40° C. and stirred for 3 hours at that temperature, cooled and stirred overnight at 18-20° C. The resultant orange slurry was filtered; the solid was washed with water, then repulped three times in hot methylene chloride (450 ml) and finally in water (115 ml) at 30° C. The product was dried to constant weight to afford 20.4 g of 2-chlorophenylhydrazido oxalic acid as a yellow solid (HPLC purity calculated as area percent:>99%).

Workup

  1. additionwas added dropwise to the acidic mixture through an addition funnel over a period of 30 minutes at −2 to 0° C
  2. additionwas added through an addition funnel over a period of 1 hour at −2 to 0° C
  3. customto come to room temperature
  4. custom(18-20° C.)
  5. customof 30 minutes
  6. temperatureheated to 40° C.
  7. stirringstirred for 3 hours at that temperature
  8. temperaturecooled
  9. stirringstirred overnight at 18-20° C
  10. filtrationThe resultant orange slurry was filtered
  11. washthe solid was washed with water
  12. customat 30° C
  13. customThe product was dried to constant weight

Sources & evidence

ORD record
ord-08e4a3bd0ffc417c80a9d765f390ba6f
Source dataset
uspto-grants-2004_06
Patent number
US06753334B2

Reaction notes

Loading…