4-Chloronaphthylamine → HCID 23514381, Verbindung

HRID 353600

Reaktionsgleichung

Reaktionsgleichung von HRID 353600
[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[CH3:2].[NH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([Cl:28])=[CH:20][CH:19]=1.[BH4-].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.CO>[Cl:28][C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([NH:17][CH2:11][C:10]2[CH:13]=[CH:14][C:7]([O:6][CH2:5][CH2:4][N:3]([CH2:15][CH3:16])[CH2:1][CH3:2])=[CH:8][CH:9]=2)=[CH:19][CH:20]=1

Komponenten

7

Edukt 3

HCID 784084-ChloronaphthylamineHCID 4116744-(2-(Diethylamino)-Ethoxy)-BenzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 23514381HCID 23514381, VerbindungAusbeute 2.089,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred solution of 0.2 gram (0.0001 mole) of 4-(2-(diethylamino)ethoxy)benzaldehyde (prepared in the manner of Step A, Example 3), 0.22 gram (0.0001 mole) of 1-amino-4-chloronaphthalene (available from Aldrich Chemical Company), and one drop of p-toluenesulfonic acid monohydrate (available from Aldrich Chemical Company) in 5 mL of toluene was heated at reflux for ten hours. At the conclusion of this period, the reaction mixture was concentrated under reduced pressure, yielding a residue. The residue was taken up in 5 mL of methanol and about 0.2 grams (0.004 mole) of sodium borohydride was added. The resulting mixture was stirred at ambient temperature for about 18 hours. After this time, the mixture was quenched with water and extracted with several portions of diethyl ether. The extracts were combined, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 0.8 gram of Compound 84. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for ten hours
  3. concentrationAt the conclusion of this period, the reaction mixture was concentrated under reduced pressure
  4. customyielding a residue
  5. customAfter this time, the mixture was quenched with water
  6. extractionextracted with several portions of diethyl ether
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ab9d87d4ffa14605a878d926f1c8b7cb
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06753429B2

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