Hydrochloric Acid → 1-(3,4-Dimethoxy-1-naphthyl)-8-(4-aminophenyl)-octane

HRID 479985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479985
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29]C(=O)C)=[CH:25][CH:24]=2)[C:6]2[C:11]([C:12]=1[O:13][CH3:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=2)[C:6]2[C:11]([C:12]=1[O:13][CH3:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 226478021-(3,4-Dimethoxy-1-naphthyl)-8-(4-acetamidophenyl)-octane

Produkt 1

HCID 226477951-(3,4-Dimethoxy-1-naphthyl)-8-(4-aminophenyl)-octaneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 554.6 mg (1.28 mmol) of 1-(3,4-dimethoxy-1-naphthyl)-8-(4-acetamidophenyl)-octane in 20 mL of MeOH was mixed with 21 mL of 2N HCl. The reaction mixture was refluxed for 23 hr. Then the reaction mixture was partitioned between 75 mL of CH2Cl2 and 21 mL of 2N NaOH. The aqueous phase was extracted with CH2Cl2 (5×40 mL). The CH2Cl2 extracts were combined, dried with MgSO4, and evaporated to dryness. Column chromatography on silica gel with 1% MeOH in CH2Cl2 gave 374.6 mg (75%) of aniline 537: 1H NMR (250 MHz, CDCl3, TMS) δ 8.14 (d, J=8 Hz, 1H), 7.94 (d, J=8 Hz, 1H), 7.47 (t, J=8 Hz, 1H), 7.37 (t, J=8 Hz, 1H), 7.12 (s, 1H), 6.96 (d, J=8 Hz, 2H), 6.62 (d, J=8 Hz, 2H), 3.99 (s, 3H), 3.97 (s, 3H), 3.1-3.0 (m, 2H), 2.5-2.4 (m, 2H), 1.8-1.3 (m, 12H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 23 hr
  2. customThen the reaction mixture was partitioned between 75 mL of CH2Cl2 and 21 mL of 2N NaOH
  3. extractionThe aqueous phase was extracted with CH2Cl2 (5×40 mL)
  4. dry with materialdried with MgSO4
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-79e834295e9d4c298ddc133124ee8222
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06649587B1

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