Oxalic Acid → Oxalate

HRID 1773894Notes

Reaction equation

HRID 1773894 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([CH:23]=[CH:24][C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)=[CH:13]3)[CH2:4][CH2:3]1.[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([CH2:23][CH2:24][C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)=[CH:13]3)[CH2:4][CH2:3]1.[C:30]([O-:35])(=[O:34])[C:31]([O-:33])=[O:32]

Participants

6

Reactant 2

HCID 971Oxalic AcidHCID 86703970HCID 86703970, compound

Product 2

HCID 71081OxalateHCID 72695287HCID 72695287, compound

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(1-methylpiperidin-4-yloxy)-2-(2-thiophen-2-ylvinyl)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 111) (100 mg, 0.247 mmole) in MeOH (10 mL) is added Pd—BaSO4 (100 mg). The flask is evacuated and filled with hydrogen (balloon). The reaction mixture is stirred overnight at room temperature. The mixture is filtered over celite, the cake is washed with MeOH and the filtrate is concentrated under reduced pressure. The residue is dissolved in acetone (1 mL) and oxalic acid (1 equivalent) is added. Acetone is removed under reduced pressure to afford 4-(1-methylpiperidin-4-yloxy)-2-(2-thiophen-2-ylethyl)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene as an oxalate.

Workup

  1. customThe flask is evacuated
  2. additionfilled with hydrogen (balloon)
  3. filtrationThe mixture is filtered over celite
  4. washthe cake is washed with MeOH
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. dissolutionThe residue is dissolved in acetone (1 mL)
  7. customAcetone is removed under reduced pressure

Sources & evidence

ORD record
ord-637e23c5ff834b51bda95621e6af8f94
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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