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Hydrochloric Acid → N-cyclopropyl-3-(7-hydroxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

HRID 507004
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 507004
[CH:1]1([NH:4][C:5](=[O:27])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[C:21]([CH3:23])[C:20]4[C:15](=[CH:16][C:17]([O:24]C)=[CH:18][CH:19]=4)[C:14]3=[O:26])[CH:7]=2)[CH2:3][CH2:2]1.[I-].[Li+].Cl>N1C(C)=CC(C)=CC=1C.[OH-].[Na+]>[CH:1]1([NH:4][C:5](=[O:27])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[C:21]([CH3:23])[C:20]4[C:15](=[CH:16][C:17]([OH:24])=[CH:18][CH:19]=4)[C:14]3=[O:26])[CH:7]=2)[CH2:2][CH2:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 11710269N-cyclopropyl-3-(7-methoxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

Produkt 1

HCID 67018616N-cyclopropyl-3-(7-hydroxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 79532,4,6-Trimethylpyridine
Lösungsmittel
HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

N-cyclopropyl-3-(7-methoxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (262 mg, 0.72 mmol) and lithium iodide (174 mg) were stirred in 2,4,6-collidine (3 ml) and heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 200° C. for 1.5 hour and then allowed to cool. The reaction mixture was dissolved in 2N NaOH and then re-acidified with 2N HCl solution. The aqueous phase was extracted with ethyl acetate (×4) and the combined organic layers were concentrated. The residue was triturated with 1N HCl, the solid was collected by filtration, washed with water, diethyl ether, and air dried to give N-cyclopropyl-3-(7-hydroxy-4-methyl-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as an off white solid (207 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.09 (s, 3H), 2.24 (s, 3H), 2.86 (m, 1H), 7.00 (s, 1H), 7.31 (d, 1H), 7.48 (d, 1H), 7.62-7.65 (m, 2H), 7.74 (s, 1H), 7.85 (d, 1H), 8.45 (d, 1H), 10.04 (s, 1H); Mass Spectrum: M+H+ 349.

Aufarbeitung

  1. temperatureto cool
  2. extractionThe aqueous phase was extracted with ethyl acetate (×4)
  3. concentrationthe combined organic layers were concentrated
  4. customThe residue was triturated with 1N HCl
  5. filtrationthe solid was collected by filtration
  6. washwashed with water, diethyl ether, and air
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f1e1dbf5f39a4032b802a64ee6ee4a86
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07786115B2

Notizen zur Reaktion

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