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5-Methylisatin → Oxindole

HRID 249689
Notes
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Reaction equation

HRID 249689 reaction equation
N(C1C=C(N2CCOCC2)N=C(OCCN2CCOCC2)N=1)N.C[C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[C:28]2=O>C(O)(=O)C.C(O)C>[NH:30]1[C:31]2[C:27](=[CH:26][CH:25]=[CH:33][CH:32]=2)[CH2:28][C:29]1=[O:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 118405-MethylisatinHCID 580857314-[2-(4-Hydrazino-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholine

Product 1

HCID 321710Oxindole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

4-[2-(4-Hydrazino-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholine (80 mg; ¼ mmol) was added to a flask along with 5-methylisatin (53 mg; ⅓ mmol) and ethanol (4 mL). One drop of acetic acid was added, and the reaction was stirred overnight at 60° C. The mixture was then filtered and the precipitate was washed with ethanol (1 mL) and dried to give 5-methyl-3-{[6-morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-pyrimidin-4-yl]-hydrazono)}-1,3-dihydro-indol-2-one.

Workup

  1. filtrationThe mixture was then filtered
  2. washthe precipitate was washed with ethanol (1 mL)
  3. customdried

Sources & evidence

ORD record
ord-80fbb6712d6c4bc482b20d03dde24791
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863270B2

Reaction notes

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