Acetic Acid → HCID 23022395, compound

HRID 387494Notes

Reaction equation

HRID 387494 reaction equation
[Cl-].[Cl-].CN([CH:6]=[C:7]([CH:12]=[N+](C)C)[CH:8]=[N+](C)C)C.[NH2:16][C:17]1[CH:18]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:20]=[CH:21][CH:22]=1.C(O)(=[O:29])C>>[CH:12]([C:7]1[CH:6]=[N:16][C:17]2[C:22]([CH:8]=1)=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=2)=[O:29]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7604m-AminoacetanilideHCID 707009502-[(Dimethylamino)methylidene]-N~1~,N~1~,N~3~,N~3~-tetramethylpropane-1,3-bis(iminium) dichloride

Product 1

HCID 23022395HCID 23022395, compoundYield 86.9%

Conditions

Temperature
140 °C

Procedure

To a 6 w/w % acetic acid solution of 2-dimethylaminomethylene-1,3-bis(dimethyliminio)propane dichloride (3.2 mL, 0.75 mmol) was added N-(3-aminophenyl)acetamide (75 mg, 0.5 mmol). The mixture was refluxed at an external bath temperature of 140° C. for 2.5 hours, and the reaction mixture was cooled to room temperature and concentrated under reduced pressure. Water (3.2 mL) was added to the concentrated residue and the resulting mixture was stirred at room temperature for 1 hour. Precipitated crystals were collected by filtration, washed three times with water (1 mL) and dried under reduced pressure to obtain N-(3-formylquinolin-7-yl)acetamide (93 mg, yield: 86.9%) as white crystals.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionWater (3.2 mL) was added to the concentrated residue
  4. customPrecipitated crystals
  5. filtrationwere collected by filtration
  6. washwashed three times with water (1 mL)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-74d6127e830e44079e016c9cf84bdec4
Source dataset
uspto-grants-2013_02
Patent number
US08373007B2

Reaction notes

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