Sodium Hydroxide → HCID 136334003, compound

HRID 1520367Notes

Reaction equation

HRID 1520367 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:13][C:14]([C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1)=O)(=[O:3])[NH2:2].[OH-].[Na+]>CCO>[N+:10]([C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:13]=[C:14]([C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1)[NH:2][C:1]2=[O:3])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67297964HCID 67297964, compound

Product 1

HCID 136334003HCID 136334003, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of N-(2-carbamoyl-4-nitrophenyl)pyrazine-2-carboxamide (2.42 g, 8.43 mmol, 1.0 eq.) in EtOH (60 mL) was added NaOH (198 g, 49.5 mmol, 5.0 eq.). 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 5 by slow addition of aqueous citric acid. The resulting precipitate was collected and dried to give 2.00 g of 6-nitro-2-(pyrazin-2-yl)quinazolin-4(3H)-one as a yellow solid (88%), LCMS m/z=270.1 (M+1) (Method A) (retention time=1.36 min).

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe residue was partitioned between H2O (50 mL) and ethyl acetate (50 mL)
  3. additionThe aqueous layer was neutralized to pH 5 by slow addition of aqueous citric acid
  4. customThe resulting precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-8bada509428348abb474252545cad6c5
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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