Sodium Hydroxide → HCID 178458207, compound

HRID 1520307Notes

Reaction equation

HRID 1520307 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH3:13])[CH:7]=[CH:6][C:5]=1[NH:14][C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1)(=[O:3])[NH2:2].[OH-].[Na+]>CCO>[CH2:11]([O:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:14][C:15]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[N:2][C:1]2=[O:3])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67297989HCID 67297989, compound

Product 1

HCID 178458207HCID 178458207, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(2-carbamoyl-4-propoxy-phenyl)-nicotinamide (980 mg, 3.27 mmol) in EtOH (20 mL) was treated with NaOH (654 mg, 16.37 mmol). The resulting mixture was stirred at room temperature for 18 h. After the reaction was completed, the volatiles were removed in vacuo. The residue was partitioned between H2O (50 mL) and ethyl acetate (50 mL). The aqueous layer was neutralized to pH 7 by slowly adding aq. citric acid and then a precipitate formed. The precipitate was collected and dried to give 1.00 g of iv-a as a grey solid (quantitative yield). LCMS m/z=282.1 (M+1) (Method B) (retention time=1.60 min).

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe residue was partitioned between H2O (50 mL) and ethyl acetate (50 mL)
  3. customa precipitate formed
  4. customThe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-f103905bc88a4b2f832f876800384adc
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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