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

HRID 1049383

반응식

HRID 1049383 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 128847862,7-Naphthyridin-1-amine수율 27.8%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
115 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a428f37b2d1d426baee561648527e1a9
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382244B2

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