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Hydrochloric Acid → 3-[Bis(4-aminophenyl)methylene]-oxindole

HRID 1600879
Notes
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Reaction equation

HRID 1600879 reaction equation
C(O)(CC)(C)C.[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C:8]1=[O:16].[NH2:17][C:18]1[CH:32]=[CH:31][C:21]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)=O)=[CH:20][CH:19]=1.CC(C)([O-])C.[K+].Cl>O>[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)=[C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[NH:7][C:8]2=[O:16])=[CH:31][CH:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 64052-Methyl-2-butanolHCID 691494,4'-DiaminobenzophenoneHCID 321710OxindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 218309833-[Bis(4-aminophenyl)methylene]-oxindoleYield 15%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 ml of t-amyl alcohol were poured 12.9 g of 97% oxindole, 20.0 g of 4,4'-diaminobenzophenone, and 26.43 g of potassium-t-butoxide. By use of a Molecular Sieves 4A tower which served as a dehydrator, the resultant mixture was refluxed with heat for 12 hours. Thereafter, the reaction mixture was cooled. An aqueous solution prepared by diluting 25 g of 35% HCl with 200 g water was added. The resultant mixture was stirred for 1.5 hours while being cooled with ice, and yellow crystals that precipitated were collected by filtration. The resultant crude product was washed with acetone, to thereby obtain 4.6 g (yield 15%) of the title compound in the form of yellow crystals. The melting point and elementary analysis data are shown in Table 15, and NMR and MS spectrum data are shown in Table 16.

Workup

  1. temperaturewith heat for 12 hours
  2. temperatureThereafter, the reaction mixture was cooled
  3. customAn aqueous solution prepared
  4. additionwas added
  5. temperaturewhile being cooled with ice, and yellow crystals that
  6. customprecipitated
  7. filtrationwere collected by filtration
  8. washThe resultant crude product was washed with acetone

Sources & evidence

ORD record
ord-68cc75b55eff460a8139f8f02bffffc1
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05977130

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes