Sodium Hydroxide → 1-Isopropyl-5-dichloroacetylaminomethylisoquinoline

HRID 1156909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1156909
[C:1]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1Cl)(=O)[C:2]1[CH:7]=CC=C[CH:3]=1.C(C1C2C(=CC=CC=2)C=CN=1)(C)C.O[CH2:33][NH:34][C:35](=[O:39])[CH:36]([Cl:38])[Cl:37].[OH-].[Na+]>S(=O)(=O)(O)O.O>[CH:2]([C:1]1[C:13]2[C:12](=[C:17]([CH2:33][NH:34][C:35](=[O:39])[CH:36]([Cl:38])[Cl:37])[CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][N:9]=1)([CH3:3])[CH3:7]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 126825361-(Propan-2-yl)isoquinolineHCID 12832764N-hydroxymethyl dichloroacetamideHCID 12851815N-[2-(2-Chlorophenyl)ethyl]benzamide

Produkt 1

HCID 128327651-Isopropyl-5-dichloroacetylaminomethylisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel2×

Versuchsvorschrift

(a-2-2) Ten grams of 1-(1-benzoyloxy-1-methylethyl)-isoquinoline was dissolved in 100 ml of ethanol, and 2 g of 10% palladium-carbon was dissolved. The mixture was stirred in a stream of hydrogen at room temperature and atmospheric pressure for 24 hours. The reaction mixture was filtered through Celite, and the solvent was distilled off. Distillation under reduced pressure afforded 4.0 g of 1-isopropylisoquinoline. (b) A mixture of 9.4 g of 1-isopropylisoquinoline and 12 g of N-hydroxymethyl dichloroacetamide was dissolved in 94 g of conc. sulfuric acid and 9.5 g of 20% fuming sulfuric acid, and the solution was heated for 3 hours. The reaction mixture was poured into water, made weakly alkaline with an aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate-benzene to afford 20 g of 1-isopropyl-5-dichloroacetylaminomethylisoquinoline having a melting point of 150.7° to 151.0° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. distillationThe solvent was distilled off
  3. customthe residue was recrystallized from ethyl acetate-benzene

Quellen und Nachweise

ORD-Eintrag
ord-18cf2404fe6d4bf0b4fe6f350f652c7f
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04337256

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