Hydrazine hydrate (1:1) → 4-(3-amino-4-methoxybenzyl)-2H-phthalazin-1-one

HRID 459780

反応式

HRID 459780 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH:5]=[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=O)[O:7]1.O.[NH2:22][NH2:23]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:7])[NH:23][N:22]=1

参加物

3

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 686248893-(3-amino-4-methoxybenzylidene)-3H-isobenzofuran-1-one

生成物 1

HCID 184443744-(3-amino-4-methoxybenzyl)-2H-phthalazin-1-one収率 81.8%

実験手順

A stirred mixture of the above 3-(3-amino-4-methoxybenzylidene)-3H-isobenzofuran-1-one (1.336 g, 0.005 mol), industrial methylated spirit (20 ml) and hydrazine monohydrate (0.25 g, 0.005 mol) was heated under reflux for 1.5 hours then cooled to ambient temperature. The resulting solid was collected by filtration, washed with water (5 ml), and dried in vacuo to give 4-(3-amino-4-methoxybenzyl)-2H-phthalazin-1-one (1.15 g) as a beige solid, m.pt. 211.5–214.5° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 3.75 (s, 3H) (—OCH3), 4.15 (s, 2H) (ArCH2—), 4.75 (s, 2H) (—NH2) 6.5–6.6 (m, 2H) (2×ArH), 6.7–6.75 (m, 1H) (ArH) 7.8–8.0 (m, 3H)(3×ArH), 8.3 (d, 1H) (ArH), 12.65 (s, 1H) (CONH); m/z (M+H)+. 282, 100% purity.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water (5 ml)
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-41ec6333bd8f4bd5a103718a919560a5
出典データセット
uspto-grants-2007_03
特許番号
US07196085B2

関連ノート

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