Hydrochloric Acid → HCID 69893747, compound

HRID 353452Notes

Reaction equation

HRID 353452 reaction equation
Cl.[Br: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>[Br: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 119922-BromoanilineHCID 23668193Sodium NitriteHCID 54670067L-Ascorbic Acid

Product 1

HCID 69893747HCID 69893747, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-1 °C

Procedure

To a 250 ml flask under a nitrogen atmosphere, concentrated HCl (50 ml, 32%, 0.51 moles) was charged and cooled down to −2 to 0° C. 2-Bromoaniline (10 g, 0.058 moles) was added in one portion as a solid. The acidic suspension was re-cooled to −2 to 0° C. and sodium nitrite (4.8 g, 0.070 moles) dissolved in water (10 ml) was added dropwise to the acidic mixture through an addition funnel over a period of 40 minutes at −2 to 0° C. The resulting mixture (yellow suspension) was stirred for 1 hour at −2 to 0° C. L-Ascorbic acid (10.3 g, 0.058 moles) was then added in portions as a solid at −2 to 0° C. over a period of 45 minutes. The reaction mixture (orange suspension) was allowed to come to room temperature (18-20° C.), then heated to 40° C. and stirred for 3 hours at this temperature. A red suspension was formed. The reaction mixture was cooled and stirred for 2 hours at 0-5° C. The slurry was filtered, washed with water and dried to constant weight to afford 14.3 g of crude 2-bromophenylhydrazido oxalic acid as an orange crystalline solid.

Workup

  1. temperatureThe acidic suspension was re-cooled to −2 to 0° C.
  2. additionwas added dropwise to the acidic mixture through an addition funnel over a period of 40 minutes at −2 to 0° C
  3. customto come to room temperature
  4. custom(18-20° C.)
  5. temperatureheated to 40° C.
  6. stirringstirred for 3 hours at this temperature
  7. customA red suspension was formed
  8. temperatureThe reaction mixture was cooled
  9. stirringstirred for 2 hours at 0-5° C
  10. filtrationThe slurry was filtered
  11. washwashed with water
  12. customdried to constant weight

Sources & evidence

ORD record
ord-3d7283e2307a4b3ea678baf4efe43ccd
Source dataset
uspto-grants-2004_06
Patent number
US06753334B2

Reaction notes

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