hydroxylamine-O-sulfonic acid → HCID 15010183, compound

HRID 2209568Notes

Reaction equation

HRID 2209568 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][C:9]=2[CH:13]=O)=[CH:4][CH:3]=1.[NH2:15]OS(O)(=O)=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][C:9]=2[C:13]#[N:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acid2×HCID 157530173-(4-Chlorophenyl)-1H-pyrrole-2-carboxaldehyde

Product 1

HCID 15010183HCID 15010183, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A mixture of 0.63 g (3.1 mmol) of 3-(p-chlorophenyl)-pyrrole-2-carboxaldehyde in 10 mL of water is stirred and ice-cooled while 0.52 g (4.6 mmol) of hydroxylamine-O-sulfonic acid in 10 mL of water is slowly added. After the addition, the cooling bath is removed and the mixture is heated for 25 minutes. On cooling, the resulting solid is collected and shown, by NMR, to be a mixture of product and starting aldehyde. This mixture is reacted in the same manner with an additional 0.49 g (4.2 mmol) of hydroxylamine-O-sulfonic acid in a total of 30 mL of water. The mixture is heated at 60°-70° C. for 2 hours. The mixture is cooled and the resulting solids are collected and purified by chromatography or silica gel using 1:1 ethyl acetate hexane to give 0.40 g of pink solid, m.p. 114°-115° C.

Workup

  1. additionis slowly added
  2. additionAfter the addition
  3. customthe cooling bath is removed
  4. temperaturethe mixture is heated for 25 minutes
  5. temperatureOn cooling
  6. customthe resulting solid is collected
  7. additiona mixture of product
  8. temperatureThe mixture is heated at 60°-70° C. for 2 hours
  9. temperatureThe mixture is cooled
  10. customthe resulting solids are collected
  11. custompurified by chromatography or silica gel using 1:1 ethyl acetate hexane

Sources & evidence

ORD record
ord-d5a774f21383473b84d8b8daa2e939f9
Source dataset
uspto-grants-1995_10
Patent number
US05455263

Reaction notes

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