Reaction #80258

ord-e75f94cdfd09486eb81e090e8b1e9b65

Reaction equation

O=CC(Cl)(Cl)Cl
chloral
[Cl-].[NH3+]O
hydroxylammonium chloride
Cl
hydrochloride
Nc1ccccc1
aniline
O=C1Nc2ccccc2C1=O
isatin
→
O=C(/C=N/O)Nc1ccccc1
isonitrosoacetanilide

Reactants

O=CC(Cl)(Cl)Cl
chloral
[Cl-].[NH3+]O
hydroxylammonium chloride
Cl
hydrochloride
Nc1ccccc1
aniline
O=C1Nc2ccccc2C1=O
isatin

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otheras shown in the following reaction scheme
  2. 2
    Otheran aqueous solution obtained
  3. 3
    Otheris reacted for 0.5 to 2 hours
  4. 4
    Temperaturewith heating at 70° to 110° C.

Procedure

The isatin derivative (9) can be synthesized, for example, as shown in the following reaction scheme. That is, an aqueous solution obtained by adding chloral and hydroxylammonium chloride to hydrochloride of an aniline derivative (10) as a starting material is reacted for 0.5 to 2 hours with heating at 70° to 110° C. to give an isonitrosoacetanilide derivative, and this product is cyclized with concentrated sulfuric acid and hydrolyzed to give an isatin derivative (9). ##STR10## wherein R1A to R1D are as defined above.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05616441uspto-grants-1997_04