Oxalic acid dihydrate → HCID 178513484, Verbindung

HRID 1165818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165818
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)=[C:5]([N+:13]([O-])=O)[C:4]=1[N+:16]([O-])=O)#[N:2].[OH2:19].O.[C:21](O)(=[O:25])[C:22](O)=[O:23]>C(O)C.[Pd]>[C:1]([C:3]1[C:4]2[N:16]=[C:22]([OH:23])[C:21]([OH:25])=[N:13][C:5]=2[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)(=[O:19])[NH2:2]

Komponenten

5

Edukt 2

HCID 61373Oxalic acid dihydrateHCID 15066366HCID 15066366, Verbindung

Produkt 1

HCID 178513484HCID 178513484, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 7-cyano-1,2,3,4-tetrahydro-5,6-dinitro-naphthalene (0.18 g, 0.73 mmol) in ethanol was hydrogenated at room temperature and atmospheric pressure in the presence of 100 mg of 5% palladium-on-charcoal. The catalyst was filtered off, and the filtrate was evaporated to dryness. The solid residue was suspended in 10 ml of 1M hydrochloric acid, oxalic acid dihydrate (0.15 g, 1.2 mmol) was added, and the mixture was refluxed for 3 h. After cooling, the solid was collected and washed with water, ethanol and ether affording 80mg (42%) of the amide; m.p. > 300° C., IR(KBr):3360, 3220, 1690, 1650, 1620 cm-1;MS: m/e (relative intensity) 259 (M+,82), 242 (44), 231 (26), 214 (100).

Aufarbeitung

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated to dryness
  4. temperaturethe mixture was refluxed for 3 h
  5. temperatureAfter cooling
  6. customthe solid was collected
  7. washwashed with water, ethanol and ether affording 80mg (42%) of the amide

Quellen und Nachweise

ORD-Eintrag
ord-c8749b2fe69946e1ad88cc2bcafee162
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04912108

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