Water → Methyl 4-[(5-aminopentyl)oxy]benzoate

HRID 2216177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216177
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:6][CH:5]=1.NN.O.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:8][CH:9]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 9321Hydrazine2×HCID 11430Potassium CarbonateHCID 575322284-[5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-benzoic acid methyl ester

Produkt 1

HCID 57532225Methyl 4-[(5-aminopentyl)oxy]benzoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A suspension of 4-[5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-benzoic acid methyl ester (1 g, 2.72 mmol, Example 283. step a) and hydrazine (98.4 μL, 3.13 mmol) in MeOH:H2O (10 mL, 4:1) was heated to 65° C. for 2 hrs. Additional hydrazine was added (171 μL, 5.44 mmol) to the reaction mixture at rt. The reaction mixture was heated to 70° C. for 2 hrs then stirred overnight at rt. Potassium carbonate (30 mL, 1N aqueous) and methylene chloride (200 mL) were added to the reaction. The organic layer was dried over magnesium sulfate. The solvents were removed in vacuo to afford the title compound as a white solid (500 mg, 77%). 1H-NMR (CDCl3): δ 7.95–8.00 (m, 2H), 6.88–6.92 (m, 2H), 4.02 (t, 2H, J=6.43 Hz), 3.88 (s, 3H), 2.71–2.76 (m, 2H), 1.79–1.86 (m, 2H), 1.49–1.56 (m, 4H).

Aufarbeitung

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. customThe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-acad8a3ed44c4842aae9fb42fb09053a
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109354B2

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