Ammonia → 1-(3-Methylanilino)-4-(4-pyridylmethyl)phthalazine

HRID 1057700

反応式

HRID 1057700 の反応式
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl.C(N(CC)CC)C.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=1.[N:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41](=O)[NH:40][N:39]=2)=[CH:33][CH:32]=1.CN(C)C(=O)N(C)C.N>O.ClCCl>[CH3:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[NH:23][C:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:38]([CH2:37][C:34]2[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=2)=[N:39][N:40]=1

参加物

9

反応物 6

HCID 222AmmoniaHCID 7934m-ToluidineHCID 11130Triethylamine hydrochlorideHCID 12437TetramethylureaHCID 14812Phosphorus oxide (P4O10)HCID 7899544-(4-Pyridylmethyl)-1(2H)-phtalazinone

生成物 1

HCID 64193871-(3-Methylanilino)-4-(4-pyridylmethyl)phthalazine

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
200 °C

実験手順

A mixture of 2.39 g (16,8 mmol) phosphorus pentoxide, 2.31 g (16,8 mmol) triethylamine hydrochloride, and 1.82 ml (16.8 mmol) m-toluidine is heated and stirred in a nitrogen atmosphere at 200° C. until a homogeneous melt has formed. To the melt, 1 g (4.2 mmol) 4-(4-pyridylmethyl)-1(2H)-phthalazinone is added and the reaction mixture stirred for a further 3.5 h at 205° C. After cooling to about 170° C., 4 ml tetramethylurea is added to the reaction mixture, followed by 2 ml water at about 110° C. The mixture is stirred for a further 30 min while cooling to RT and then distributed between dichloromethane and a mixture of 20 ml water and 5 ml conc. ammonia. The organic phase dried over sodium sulfate is concentrated by evaporation and the residue purified on silica gel by flash chromatography using acetate and acetate/methanol (99:1 and 19:1). Title compound is obtained after crystallization of the product-containing fractions from acetonitrile and subsequent recrystallization from acetate; m.p. 141-143° C.; ESI-MS: (M+H)+=327.

後処理

  1. temperatureis heated
  2. customhas formed
  3. stirringthe reaction mixture stirred for a further 3.5 h at 205° C
  4. temperatureAfter cooling to about 170° C.
  5. stirringThe mixture is stirred for a further 30 min
  6. temperaturewhile cooling to RT
  7. dry with materialThe organic phase dried over sodium sulfate
  8. concentrationis concentrated by evaporation
  9. customthe residue purified on silica gel by flash chromatography

出典と根拠

ORDレコード
ord-1e794733e22b4bffa9659de9ed27b495
出典データセット
uspto-grants-2003_02
特許番号
US06514974B2

関連ノート

読み込み中…