Acetic Acid → 2,7-Naphthyridin-1-amine

HRID 1049383

反応式

HRID 1049383 の反応式
C([O-])=O.[NH4+].C[N:6](C)/[CH:7]=[CH:8]/[C:9]1[C:14]([C:15]#[N:16])=[CH:13][N:12]=[CH:11][CH:10]=1.CC(O)=O>O>[C:15]1([NH2:16])[C:14]2[C:9](=[CH:10][CH:11]=[N:12][CH:13]=2)[CH:8]=[CH:7][N:6]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 2723923Ammonium formateHCID 124604474-((1E)-2-(Dimethylamino)ethenyl)-3-pyridinecarbonitrile

生成物 1

HCID 128847862,7-Naphthyridin-1-amine収率 27.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
115 °C

実験手順

810 g of ammonium formate are added to 253 g of 4-((E)-2-dimethylaminovinyl)nicotinonitrile in a 4 liter vessel. 300 ml of AcOH are then added, and the mixture is heated at 115° C. for 20 h. The mixture is cooled, 5 liters of water are added, and the mixture is extracted 10× with 0.5 liter of CH2Cl2. The aqueous phase is adjusted to ˜pH 10 using 160 g of NaOH. The aqueous phase is extracted with MTB ether, the organic phase is separated off and dried over sodium sulfate. Removal of the solvent and drying gives 59 g of 2,7-naphthyridin-1-ylamine, M˜145.16 g/mol, M+H found 146, NMR corresponds.

後処理

  1. temperatureThe mixture is cooled
  2. extractionthe mixture is extracted 10× with 0.5 liter of CH2Cl2
  3. extractionThe aqueous phase is extracted with MTB ether
  4. customthe organic phase is separated off
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent
  7. customdrying

出典と根拠

ORDレコード
ord-a428f37b2d1d426baee561648527e1a9
出典データセット
uspto-grants-2016_07
特許番号
US09382244B2

関連ノート

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