Nitric Acid → 6-Nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acid

HRID 2052660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2052660
[NH:1]([C:5]1[C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[C:8]([C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C(OC(=O)C)(=O)C.[N+:25]([O-:28])([OH:27])=[O:26]>C(O)(=O)C>[N+:25]([C:6]1[CH:7]=[C:8]([C:15]([OH:17])=[O:16])[C:9]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[C:5]=1[NH:1][C:2]([CH3:4])=[O:3])([O-:27])=[O:26].[N+:25]([C:7]1[CH:6]=[C:5]([NH:1][C:2]([CH3:4])=[O:3])[C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[C:8]=1[C:15]([OH:17])=[O:16])([O-:28])=[O:26]

Komponenten

6

Edukt 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 149562078-Acetamido-1,4-benzodioxan-5-carboxylic acid

Produkt 2

HCID 205447176-Nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acidHCID 205447477-Nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel3×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

42 g of 8-acetamino-1,4-benzodioxane-5-carboxylic acid, 75 ml of acetic acid and 75 ml of acetic anhydride were introduced into a balloon flask and then a solution of 17.5 ml of nitric acid (d=1.49) in 17 ml of acetic acid was added, with the temperature being left rising. After dissolution and crystallization, 50 ml of acetic acid were added. The mixture was agitated at 40°-45° C. and then cooled to 20° C. The precipitate was dried off, washed with acetic acid and water and dried. 13.5 g of a 50% mixture of 7-nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acid and 6-nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acid were obtained. The 7-nitro-8-acetamino-1,4-benzodioxane-5-carboxylic acid was separated and then treated according to the process of Example 31 with isobutyl chloroformate and diethylaminoethylamine. N-(diethylaminoethyl)-7-nitro-8-acetamino-1,4-benzodioxane-5-carboxamide was obtained. The structure was confirmed by nuclear magnetic resonance analysis.

Aufarbeitung

  1. waitbeing left
  2. additionwere added
  3. customThe precipitate was dried off
  4. washwashed with acetic acid and water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4e624b4973c14d4993c466454366d4ed
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04186135

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