Sodium Carbonate → 7-(3-Amino-phenylamino)-1,3-dihydro-indol-2-one

HRID 422020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 422020
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)[C:7]=1[NH2:20])C.C([O-])([O-])=O.[Na+].[Na+]>Cl>[NH2:19][C:15]1[CH:14]=[C:13]([NH:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]3[C:7]=2[NH:20][C:4](=[O:3])[CH2:5]3)[CH:18]=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 10340Sodium CarbonateHCID 59804307[2-Amino-3-(3-amino-phenylamino)-phenyl]-acetic acid ethyl ester

Produkt 1

HCID 598042847-(3-Amino-phenylamino)-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

[2-Amino-3-(3-amino-phenylamino)-phenyl]-acetic acid ethyl ester (0.50 g, 1.7 mmol) is refluxed in 1 N hydrochloric acid for 30 minutes. The reaction mixture is cooled to room temperature and basified with saturated Na2CO3. The mixture is then extracted with ethyl acetate (30 ml×3). The organic layers are combined, dried with Na2SO4 and concentrated. The residue is purified by flash column chromatography (silica gel, eluted with ethyl acetate-methanol with 0.5% NH3) to give the desired compound. 1H NMR (DMSO-d6) δ 4.93 (s, 2H), 6.06 (d, 1H, J=6.8 Hz), 6.14 (d, 1H, J=8.0 Hz), 6.21 (s, 1H), 6.78 (d, 1H, J=7.2 Hz), 6.85 (t, 2H, J=8.0 Hz), 6.97 (s, 1H), 7.05 (d, 1H, J=8.0 Hz), 9.96 (s, 1H); LC-MS: 240.1 (MH+).

Aufarbeitung

  1. extractionThe mixture is then extracted with ethyl acetate (30 ml×3)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash column chromatography (silica gel, eluted with ethyl acetate-methanol with 0.5% NH3)

Quellen und Nachweise

ORD-Eintrag
ord-81131d3816204f98a5e4bfbc4543152f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101608B2

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