Sodium Hydroxide → 2-Amino-3-(pyrazine-2-carboxamido)benzoic acid

HRID 520447Notes

Reaction equation

HRID 520447 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:13]([NH:14][C:15]([C:17]2[CH:22]=[N:21][CH:20]=[CH:19][N:18]=2)=[O:16])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>C1COCC1>[NH2:3][C:4]1[C:13]([NH:14][C:15]([C:17]2[CH:22]=[N:21][CH:20]=[CH:19][N:18]=2)=[O:16])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58552889Methyl 2-amino-3-(pyrazine-2-carboxamido)benzoate

Product 1

HCID 585528702-Amino-3-(pyrazine-2-carboxamido)benzoic acidYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of aq NaOH (20 mL, 88.2 mmol) and methyl 2-amino-3-(pyrazine-2-carboxamido)benzoate 15 (1.2 g, 4.41 mmol) in THF (20 mL) was stirred at room temperature for 4 h. The volatiles were evaporated and the pH adjusted to 4 using aq HCl. The resulting precipitate was collected by filtration, rinsed with H2O and dried under vacuum to give 16 (750 mg, 66% yield).

Workup

  1. customThe volatiles were evaporated
  2. filtrationThe resulting precipitate was collected by filtration
  3. washrinsed with H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-156128958e184f0ba782fce0ade9fb49
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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