Sulfuric Acid → 5-Methylisatin

HRID 1470602Notes

Reaction equation

HRID 1470602 reaction equation
ON=[CH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=[O:5].[OH:14]S(O)(=O)=O>>[CH3:13][C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][CH:11]=1)[NH:6][C:4](=[O:5])[C:3]2=[O:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 6708874HCID 6708874, compound

Product 1

HCID 118405-Methylisatin

Procedure

2-Hydroxyimino-N-p-tolyl-acetamide (14 g, 0.0078 mol) was added portion wise to a preheated (60° C.) conc. H2SO4 (70 mL) over a period of 30 min. After the addition, the mixture was stirred at the same temperature for another 1 h. The reaction mixture was cooled to room temperature and was poured into crushed ice. The precipitate was collected by filtration and washed with chilled water several times. Finally it was dried in a vacuum oven to get the required product as brick red coloured solid.

Workup

  1. additionAfter the addition
  2. additionwas poured
  3. custominto crushed ice
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with chilled water several times
  6. customFinally it was dried in a vacuum oven

Sources & evidence

ORD record
ord-6fd788cb9eb84e4a88b7b8513f72706d
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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