Water → HCID 178479589, compound

HRID 2291595Notes

Reaction equation

HRID 2291595 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=O)[C:7](=[O:28])[N:8]2[CH2:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([N:20]=CC3C=CC=CC=3)[CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32].O>C(#N)C.Cl>[ClH:1].[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[N:31][OH:32])[C:7](=[O:28])[N:8]2[CH2:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([NH2:20])[CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 54331391HCID 54331391, compound

Product 1

HCID 178479589HCID 178479589, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 6-chloro-1-[(4-benzylideneamino-1-piperazinyl)carbonylmethyl]-2,3-indolinedione (1.5 g) and hydroxylamine hydrochloride (2.5 g) in acetonitrile (100 ml), conc. hydrochloric acid (50 ml), and water (50 ml) was heated at 40° C. for 2 hour. The reaction mixture was concentrated up to 20 ml and the precipitates appeared were filtered, and air-dried. This crude material was recrystallized from aqueous methanol at first, and for water finally to give 6-chloro-1-[(4-amino-1-piperazinyl)carbonylmethyl]-3-hydroxyimino-2-indolinone hydrochloride (0.54 g).

Workup

  1. concentrationThe reaction mixture was concentrated up to 20 ml
  2. filtrationthe precipitates appeared were filtered
  3. customair-dried
  4. customThis crude material was recrystallized from aqueous methanol at first, and for water finally

Sources & evidence

ORD record
ord-8ec3d862df5045d2b5bcef9bed933db2
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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