4-Aminoacetanilide → 1-(4-Acetaminoanilino)-4-(4-pyridylmethyl)phthalazine

HRID 49862

反応式

HRID 49862 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[CH3:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)=[O:21]>C(O)CCC>[NH:22]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)=[CH:25][CH:24]=1)[C:20]([CH3:19])=[O:21]

参加物

4

反応物 2

HCID 312304-AminoacetanilideHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

生成物 1

HCID 227419571-(4-Acetaminoanilino)-4-(4-pyridylmethyl)phthalazine

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
110 °C

実験手順

A mixture of 0.511 g (2 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine, 0.901 g (6 mmol) 4-aminoacetanilide and 5 ml 1-butanol is heated for 3 h at 110° C. The reaction mixture is then evaporated under vacuum, the crystalline residue is taken up in a mixture of 20 ml dichloromethane and 10 ml 20% aqueous potassium carbonate solution while stirring, then filtered and the filter residue washed with water and dichloromethane. After recrystallization from dichloromethane/methanol and drying under HV (8 h, 100° C.), title compound is obtained with a methanol content of 1.27%; m.p. >270° C.; 1H NMR (DMSO-d6) 9.91 (s, 1H), 9.13 (s, 1H), 8.59-8.64 (m, 1H), 8.48 (d, 2H), 8.08-8.13 (m, 1H), 7.91-8.01 (m, 2H), 7.85 (d, 2H), 7.58 (d, 2H), 7.32 (d, 2H), 4.58 (s, 2H), 2,05 (s, 3H), [methanol: 4.13 (q, 0.15H), 3.19 (d, 0.45H)]; ESI-MS: (M+H)+=370.

後処理

  1. customThe reaction mixture is then evaporated under vacuum
  2. additionthe crystalline residue is taken up in a mixture of 20 ml dichloromethane and 10 ml 20% aqueous potassium carbonate solution
  3. filtrationfiltered
  4. washthe filter residue washed with water and dichloromethane
  5. customAfter recrystallization from dichloromethane/methanol
  6. customdrying under HV (8 h, 100° C.)

出典と根拠

ORDレコード
ord-00f06d4ab1d24d15b267718d87e9d089
出典データセット
uspto-grants-2004_03
特許番号
US06710047B2

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