Oxalic Acid → HCID 42606391, compound

HRID 885466Notes

Reaction equation

HRID 885466 reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][CH2:5][C:6]1([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:14]2[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH2:8][O:7]1.[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28]>C(O)C>[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28].[CH3:25][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:14]2[C:9](=[CH:10][C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH2:8][O:7]1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 426063901148027-74-0

Product 1

HCID 42606391HCID 42606391, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.3 g (24.7 mmol) of the 1-{3-(dimethylamino)propyl}-1-(4-methoxyphenyl)-1,3-dihydro-5-isobenzofurancarbonitrile prepared in Example 1 was dissolved in 85 ml of ethanol, and 3.4 g (27.2 mmol) of oxalic acid was slowly added at room temperature. The solution was stirred at room temperature for 0.5 hr, and it was cooled to 0° C. and further stirred for 1 hr. The solution was filtered to recover the precipitate. The precipitate was washed with hexane and dried to afford 7.1 g of the target compound as a white solid (yield: 67%).

Workup

  1. temperatureit was cooled to 0° C.
  2. stirringfurther stirred for 1 hr
  3. filtrationThe solution was filtered
  4. customto recover the precipitate
  5. washThe precipitate was washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-741f5bda399444ab88b968de23ed4b4c
Source dataset
uspto-grants-2012_08
Patent number
US08242159B2

Reaction notes

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