Sodium Hydroxide → HCID 178422428, compound

HRID 1520378Notes

Reaction equation

HRID 1520378 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=2)=[C:4]([C:18](=[O:20])[NH2:19])[CH:3]=1.[OH-].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[C:6]([CH3:8])[CH:7]=1)[N:9]=[C:10]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[N:19]=[C:18]2[OH:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67298051HCID 67298051, compound

Product 1

HCID 178422428HCID 178422428, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(4-bromo-2-carbamoyl-6-methylphenyl)nicotinamide (1.74 g salt, 5.22 mmol, 1.0 eq) in EtOH (50 mL) was treated with NaOH (1.04 g, 26.1 mmol, 5.0 eq). The resulting mixture was stirred at room temperature overnight. After the reaction was completed, the volatiles were removed in vacuo. Water (30 mL) was added to the residue and the mixture was adjusted to pH˜1 or 2 by slow addition of aqueous HCl. The resultant precipitate was collected and dried to give 870 mg of iv-h as a yellow solid (77% yield after two steps), LCMS m/z=315.7, 317.7 (M+1) (Method B) (retention time=1.74 min).

Workup

  1. customthe volatiles were removed in vacuo
  2. additionWater (30 mL) was added to the residue
  3. additionthe mixture was adjusted to pH˜1 or 2 by slow addition of aqueous HCl
  4. customThe resultant precipitate was collected
  5. customdried
  6. customto give 870 mg of iv-h as a yellow solid (77% yield after two steps), LCMS m/z=315.7, 317.7 (M+1) (Method B) (retention time=1.74 min)

Sources & evidence

ORD record
ord-c10466b7dbab4970bf90bda1f1676138
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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