تفاعل #685030

ord-be612bfc945f485883ab99c4aca91ea9

معادلة التفاعل

[Na+].[OH-]
NaOH
CCOC(=O)CCc1c(/C=C2\C(=O)Nc3ccccc32)[nH]c2c1C(=O)CCC2
(Z)-3-((3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1 H-indol-2-yl)methylene)indolin-2-one
Cl
HCl
O=C(O)CCc1c(/C=C2\C(=O)Nc3ccccc32)[nH]c2c1C(=O)CCC2
desired product
O=C(O)CCc1c(/C=C2\C(=O)Nc3ccccc32)[nH]c2c1C(=O)CCC2
(Z)-3-((3-carboxyethyl-4-oxo-4,5,6,7-tetrahydro-1 H-indol-2-yl)methylene)indolin-2-one

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe reaction was heated
  2. 2
    درجة الحرارةat reflux for 2.0 h
  3. 3
    ترشيحThe resultant precipitate was filtered
  4. 4
    غسيلwashed with MeOH

الإجراء التجريبي

To an EtOH solution (3.0 mL) containing (Z)-3-((3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1 H-indol-2-yl)methylene)indolin-2-one (0.50 mmol) was added 3.0 N aqueous NaOH (1.0 mL). The reaction was heated at reflux for 2.0 h and cooled to room temperature. The solution was acidified with 6 N HCl to pH 3.0. The resultant precipitate was filtered and washed with MeOH to provide the desired product. 1 H NMR (DMSO-d6) δ 13.76 (s, 1 H), 11.01 (s, 1 H), 7.77 (s, 1 H), 7.76 (d, 1 H), 7.17 (dd, 1 H), 7.01 (dd, 1 H), 6.89 (dd, 1 H), 3.15 (t, 2 H), 2.91 (t, 2H), 2.36-2.41 (m, 2 H), 2.06 (t, 2 H).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07897602B2uspto-grants-2011_03