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Hydrochloric Acid → 5-(N-formyl-N-methylamino-methyl)isatoic anhydride

HRID 1037818
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1037818
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH:26]=[O:27])[CH3:25])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].Cl>CN(C)C=O>[CH:26]([N:24]([CH2:23][C:20]1[CH:19]=[C:15]2[C:16]([O:18][C:1](=[O:2])[NH:13][C:14]2=[CH:22][CH:21]=1)=[O:17])[CH3:25])=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 580183122-amino-5-(N-formyl-N-methylamino-methyl)benzoic acid

Produkt 1

HCID 251343765-(N-formyl-N-methylamino-methyl)isatoic anhydride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

There was suspended, in 15.2 mL of N,N-dimethylformamide, 3.82 g of 1,1′-carbonyl-diimidazole (CDI) and the resulting suspension was cooled to 5° C. To this slurry, there was added 4.0 g of 2-amino-5-(N-formyl-N-methylamino-methyl)benzoic acid in two portions, followed by the stirring of the same for one hour. After the confirmation of the disappearance of the starting material by HPLC, seed crystals were added to the slurry while dropwise adding 40.3 mL of a 1M hydrochloric acid aqueous solution to separate out solid and the resulting solid was isolated through filtration under reduced pressure. After washing the solid with 120 mL of water, it was dried at 70° C. for 13 hours under reduced pressure to thus give 3.20 g of the title compound as a white solid.

Aufarbeitung

  1. additionAfter the confirmation of the disappearance of the starting material by HPLC, seed crystals were added to the slurry
  2. customto separate out solid
  3. customthe resulting solid was isolated through filtration under reduced pressure
  4. washAfter washing the solid with 120 mL of water, it
  5. dry with materialwas dried at 70° C. for 13 hours under reduced pressure to thus give 3.20 g of the title compound as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-6823eb923127454f87b2214ab18daea5
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546610B2

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