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4-Chloroaniline → HCID 86698996, Verbindung

HRID 2272255
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2272255
[CH:1]1([C:4]2[C:5]([N+:15]([O-:17])=[O:16])=[CH:6][C:7]([N+:12]([O-:14])=O)=[C:8]([CH:11]=2)[CH:9]=O)[CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.[C-:26]#[N:27].[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C.CO>[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:9]([C:26]#[N:27])=[C:8]3[C:7]([CH:6]=[C:5]([N+:15]([O-:17])=[O:16])[C:4]([CH:1]4[CH2:2][CH2:3]4)=[CH:11]3)=[N+:12]2[O-:14])=[CH:21][CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 78124-ChloroanilineHCID 7918Acetic AnhydrideHCID 8929Sodium Cyanide2×HCID 866664205-Cyclopropyl-2,4-dinitrobenzaldehyde

Produkt 1

HCID 86698996HCID 86698996, VerbindungAusbeute 108,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred suspension of (iv) (20 g, 0.09 mol) in acetic acid (400 mL) was added 4-chloroaniline (21.6 g, 0.17 mol) and the reaction heated at 60° C. to obtain a complete solution. To this solution was added sodium cyanide (20 g, 0.41 mol) portionwise over 20 min. The reaction mixture was stirred for 5 min whereupon acetic anhydride (6 mL) was added. Upon the formation of a precipitate, an additional quantity of sodium cyanide (20 g, 0.41 mol) was added portionwise. After stirring for 1 h, the reaction mixture was cooled to RT, diluted with MeOH (30 ml) and the solids separated by filtration. The solid cake was dissolved in chloroform (400 ml) and the organics washed with water (2×100 ml), dried (MgSO4) and concentrated in vacuo to give the intermediate 2-(4-chlorophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrile 1-oxide (34.6 g). ESI-MS m/z calculated for [M+H]+: 355.1. found: 355.2. 1H NMR (400 MHz, CDCl3) δ 8.32 (s, 1H), 7.72-7.50 (m, 5H), 2.44-2.30 (m, 1H), 1.18-1.05 (m, 2H), 0.85-0.71 (m, 2H).

Aufarbeitung

  1. customto obtain a complete solution
  2. additionwas added
  3. temperaturethe reaction mixture was cooled to RT
  4. customthe solids separated by filtration
  5. dissolutionThe solid cake was dissolved in chloroform (400 ml)
  6. washthe organics washed with water (2×100 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8b1cefaa4dbe4dada3f2cea2ce127016
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09120775B2

Notizen zur Reaktion

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