Hydrochloric Acid → HCID 178510679, Verbindung

HRID 255000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 255000
FC1C=C(C=CC=1)N.Cl.N([O-])=O.[Na+].O=C1C2C(=CC=CC=2)C(=O)N1CC(=O)CC#N.CC([O-])=O.[Na+].[NH2:36][C:37]1[C:38](=[N:54][NH:55][C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([F:62])[CH:57]=2)[C:39]([CH2:42][N:43]2C(=O)C3C(=CC=CC=3)C2=O)=[N:40][N:41]=1.NN>O.CN(C=O)C.O.C(O)C>[NH2:43][CH2:42][C:39]1[C:38](=[N:54][NH:55][C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([F:62])[CH:57]=2)[C:37]([NH2:36])=[N:41][N:40]=1

Komponenten

11

Edukt 7

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 97423-FluoroanilineHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 668449574-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-3-oxobutyronitrileHCID 178509152HCID 178509152, Verbindung

Produkt 1

HCID 178510679HCID 178510679, VerbindungAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of 3-fluoroaniline (1.67 g, 15 mmole) in 17 mL of water, acidified with 3.75 mL of conc. HCl (45 mmole) in an ice bath, was treated with NaNO2 (1.35 g, 19.5 mmole). The diazonium solution was then added to the solution of 4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-oxobutyronitrile (2.28 g, 10 mmole) with NaOAc (6.12 g, 45 mmole) in DMF/water mixture (30:35 mL). From this reaction, 3.4 g of 2-{5-amino-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylmethyl}isoindole-1,3-dione, as a yellow powder, was obtained, which was then treated with hydrazine (22 mmole) portionwise in hot ethanol. After the reaction was completed, a few grams of silica gel was mixed and the solvent was evaporated. The powdery residue was purified by column chromatography (CH2Cl2:MeOH:NH3.H2O=600:150:6) to yield 1.5 g (61%) of the title compound as an orange powder. 1H NMR (ppm, 200 MHz, DMSO-d6) δ 7.40-7.70 (m, 3H), 7.12 (m, 1H), 7.00 (br s, 2H), 4.01 (s, 2H).

Aufarbeitung

  1. customas a yellow powder, was obtained
  2. additiona few grams of silica gel was mixed
  3. customthe solvent was evaporated
  4. customThe powdery residue was purified by column chromatography (CH2Cl2:MeOH:NH3.H2O=600:150:6)

Quellen und Nachweise

ORD-Eintrag
ord-782c6a7f13db494b810a81dddfdb6932
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875728B2

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