1,4-Dioxane hydrochloride → HCID 178478857, compound

HRID 902448Notes

Reaction equation

HRID 902448 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[CH2:10][NH:11]C(=O)OCC1C=CC=CC=1.[ClH:22].O1CCOCC1>CC(O)=O.CO.O1CCOCC1.[Pd]>[Cl-:22].[Cl-:22].[NH3+:11][CH2:10][C:2]1[NH:3][C:4]2=[NH+:5][CH:6]=[CH:7][CH:8]=[C:9]2[N:1]=1

Participants

6

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178523089HCID 178523089, compound

Product 1

HCID 178478857HCID 178478857, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolventHCID 10129899Acetic acid methanolSolvent

Procedure

To a mixture of 2-4 (52 g, 151.88 mmol) in 1000 mL of 1:1 AcOH/MeOH was added 20 g 10% Pd/C. The reaction mixture was stirred under 1 atm H2 for 20 hours. The mixture was filtered through a celite pad, concentrated, and then azeotroped with dioxane to give tan oil. The semisolid or thick oil was suspended in 200 mL dioxane and 200 mL 4.0 M HCl/dioxane was added to produce a tan suspension. The solid was collected, washed with dioxane (200 mL) and dried in vacuo to give 2-5 as a tan solid. 1H NMR (500 MHz, CD3OD) 8.75 (d, 1H, J=8 Hz), 8367 (d, 1H, J=6 Hz), 7.85 (m, 1H), 4.88 (s, 2H). HRMS (ES, M+1) calc'd 149.0822. found 149.0812.

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. concentrationconcentrated
  3. customazeotroped with dioxane
  4. customto give tan oil
  5. customto produce a tan suspension
  6. customThe solid was collected
  7. washwashed with dioxane (200 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-0587a4ad055e49579500e9f3d439fae3
Source dataset
uspto-grants-2008_04
Patent number
US07365202B2

Reaction notes

Loading…