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

HRID 1049383Notes

Reaction equation

HRID 1049383 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a428f37b2d1d426baee561648527e1a9
Source dataset
uspto-grants-2016_07
Patent number
US09382244B2

Reaction notes

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