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

HRID 49885
ノート
印刷プレビュー

反応式

HRID 49885 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
参加物反応条件実験手順後処理出典と根拠反応ノート

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 6419387
1-(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-2d57d14ff339450ebd4864938eadbeb0
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06710047B2

反応ノート

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