Acetic Acid → HCID 15406816, compound

HRID 1533002Notes

Reaction equation

HRID 1533002 reaction equation
[Cl:1][C:2]1[C:3]([C:20]#[N:21])=[C:4]2[N:9]([C:10]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:8][CH2:7][C:6](Cl)(Cl)[C:5]2=[O:19].C(O)(=O)C>C(O)C.[Pd]>[Cl:1][C:2]1[C:3]([C:20]#[N:21])=[C:4]2[N:9]([C:10]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:8][CH2:7][CH2:6][C:5]2=[O:19]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22012005HCID 22012005, compound

Product 1

HCID 15406816HCID 15406816, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of 10.14 g of 2,7,7-trichloro-8-oxo-3-pyridin-3-yl-5,6,7,8-tetrahydroindolizine-1-carbonitrile and 300 cm3 of acetic acid in 1000 cm3 of ethanol is stirred under argon, and 3.06 g of 10% palladium on carbon in 50 cm3 of ethanol are added. The reaction mixture is bubbled with hydrogen for 2 hours at room temperature, and then filtered on No. 3 sintered glass covered with Celite. The cake is washed with twice 50 cm3 of ethanol and the filtrate is then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature close to 55° C. An oily residue is taken up in 150 cm3 of water and the pH is brought to 8-9 by addition of sodium hydrogen carbonate. 7.08 g of 2-chloro-8-oxo-3-pyridin-3-yl-5,6,7,8-tetrahydroindolizine-1-carbonitrile are obtained in the form of a white solid melting at a temperature greater than 260° C.

Workup

  1. customThe reaction mixture is bubbled with hydrogen for 2 hours at room temperature
  2. filtrationfiltered on No
  3. washThe cake is washed with twice 50 cm3 of ethanol
  4. concentrationthe filtrate is then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature
  5. customclose to 55° C
  6. additionthe pH is brought to 8-9 by addition of sodium hydrogen carbonate

Sources & evidence

ORD record
ord-964ef4c2ec564d5e993564056ab02683
Source dataset
uspto-grants-2001_03
Patent number
US06207675B1

Reaction notes

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