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

HRID 723222ノート

反応式

HRID 723222 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f62e0e6e1c2a4c66b54ef3d7dbe78fab
出典データセット
uspto-grants-2006_11
特許番号
US07138530B2

反応ノート

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