Sulfuric Acid → 4,6-Dichloroisatin

HRID 1095519Notes

Reaction equation

HRID 1095519 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])[CH:11]=NO)[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(=O)(=O)(O)[OH:16]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]2[C:3]=1[C:11](=[O:16])[C:10](=[O:14])[NH:9]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 71353147N-(3,5-Dichlorophenyl)-2-(hydroxyimino)acetamide

Product 1

HCID 2519084,6-DichloroisatinYield 81%

Conditions

Temperature
90 °C

Procedure

The N-(3,5-dichlorophenyl)-2-hydroxyiminoacetamide just prepared (12.1 g, 0.052 mol) was added to 96 per cent strength sulfuric acid (56 ml) at 50-75° C. in the course of 15 min. The reaction mixture was then heated at 90° C. for 15 min, while stirring. After cooling, the mixture was poured slowly on to ice (500 g). The solid formed was filtered off with suction after 30 min. The desired isatin was isolated in a yield of 81% (9.12 g) as an orange-coloured solid. It was not possible to determine a melting point.

Workup

  1. temperatureAfter cooling
  2. customThe solid formed
  3. filtrationwas filtered off with suction after 30 min

Sources & evidence

ORD record
ord-1945cd6d6fdf4c8a945f9b5cb2a0e64c
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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