5-Amino-1-naphthol → 4-Fluoro-N-(5-hydroxynaphthalen-1-yl)-3-nitrobenzamide

HRID 326169

Reaktionsgleichung

Reaktionsgleichung von HRID 326169
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7](Cl)=[O:8])([O-:3])=[O:2].[NH2:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[C:20]2[OH:25]>C(#N)C.CN(C)C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7]([NH:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[C:20]2[OH:25])=[O:8])([O-:3])=[O:2]

Komponenten

5

Edukt 2

HCID 657465-Amino-1-naphtholHCID 27833474-Fluoro-3-nitrobenzoyl chloride

Produkt 1

HCID 204625984-Fluoro-N-(5-hydroxynaphthalen-1-yl)-3-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 949N,N-DimethylanilineLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

22.4 g of 3-nitro-4-fluorobenzoyl chloride (0.12 mols) were added dropwise at 0° C. to a suspension of 19.1 g of 5-amino-1-naphthol (0.12 mols) in 120 ml of acetonitrile and 14.2 g of N,N-dimethylaniline. The mixture was further stirred until it reached room temperature, and then heated for 30 minutes at 50° C. The yellow deposit was suction filtered and washed with acetonitrile. The deposit was dissolved in tetrahydrofurane and stirred with charcoal, filtered and the product was precipitated from the filtrate with petrol 50/75. Yield: 25.8 g=66% of the theoretical yield; mp. 235°-238° C.

Aufarbeitung

  1. customreached room temperature
  2. filtrationThe yellow deposit was suction filtered
  3. washwashed with acetonitrile
  4. dissolutionThe deposit was dissolved in tetrahydrofurane
  5. stirringstirred with charcoal
  6. filtrationfiltered
  7. customthe product was precipitated from the filtrate with petrol 50/75

Quellen und Nachweise

ORD-Eintrag
ord-6d33a443335a4931be334c29a34512c5
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04444867

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