HCID 11538568, compound → Isatin

HRID 1867923Notes

Reaction equation

HRID 1867923 reaction equation
CN(C)S(C1C=CC([C:12]2[C:13]3CCN(C)C[C:18]=3[C:19]3[NH:24][C:23](=[O:25])[C:22](=[O:26])[C:20]=3[CH:21]=2)=CC=1)(=O)=O.ON=C1C2C=C(C3C=CC(S(N(C)C)(=O)=O)=CC=3)C3CCN(C)CC=3C=2NC1=O>>[NH:24]1[C:19]2[C:20](=[CH:21][CH:12]=[CH:13][CH:18]=2)[C:22](=[O:26])[C:23]1=[O:25]

Participants

3

Reactant 2

HCID 11538568HCID 11538568, compoundHCID 178480008HCID 178480008, compound

Product 1

HCID 7054IsatinYield 67%

Procedure

The reaction mixture (i.e. N,N-dimethyl-4-(8-methyl-2,3-dioxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-h]isoquinolin-5-yl)-benzenesulfonamide and 4-(3-hydroxyimino-8-methyl-2-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-h]isoquinolin-5-yl)-N,N-dimethyl-benzenesulfonamide) was poured onto H2O (3.5 L), heated to reflux and then filtered warm to remove celite. The celite was washed with boiling water (750 mL), and the combined aqueous fractions allowed cooling slowly overnight for precipitation. The precipitate was filtered off, washed with H2O (2×250 mL) and 96% EtOH (2×250 mL) and then air dried to give 69.8 g (67%) of crude isatin derivative as the hydrosulfate. The crude product contained 11.4% (typically 9-13%) of the oxime.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. filtrationfiltered
  4. temperaturewarm
  5. customto remove celite
  6. washThe celite was washed with boiling water (750 mL)
  7. temperaturethe combined aqueous fractions allowed cooling slowly overnight for precipitation
  8. filtrationThe precipitate was filtered off
  9. washwashed with H2O (2×250 mL) and 96% EtOH (2×250 mL)
  10. customair dried

Sources & evidence

ORD record
ord-3d40f1ebebcb4ebf9d8f2f66c702b360
Source dataset
uspto-grants-2009_12
Patent number
US07632948B2

Reaction notes

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