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

HRID 459780

반응식

HRID 459780 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-41ec6333bd8f4bd5a103718a919560a5
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196085B2

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