Sodium Hydroxide → HCID 69795151, compound

HRID 2181663Notes

Reaction equation

HRID 2181663 reaction equation
[NH2:1][C:2]([C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([O:15]C)=[O:14])[CH:10]=[CH:9][C:7]=2[CH:8]=1)=[O:3].[OH-].[Na+]>CO.O>[NH2:1][C:2]([C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][C:7]=2[CH:8]=1)=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22481693HCID 22481693, compound

Product 1

HCID 69795151HCID 69795151, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2-(aminocarbonyl)-1-benzofuran-6-carboxylate(164 mg, 0.75 mmol) is dissolved in MeOH (5 mL) and water (1 mL), treated drop-wise with 2N NaOH (450 μL, 0.9 mmol) and monitored by TLC. The volatiles are removed in vacuo, and the resulting tan solid is dissolved in water (5 mL) and acidified to pH 3 with concentrated HCl. The resulting solid is collected via filtration and dried in a vacuum oven with heat 50° C. to afford 142 mg (93%) of 2-(aminocarbonyl)-1-benzofuran-6-carboxylic acid as an orange solid. HRMS (EI) calcd for C10H7NO4: 205.0375, found 205.0378 (M)+.

Workup

  1. customThe volatiles are removed in vacuo
  2. dissolutionthe resulting tan solid is dissolved in water (5 mL)
  3. filtrationThe resulting solid is collected via filtration
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-7aade1f6d7e34b47b9d9c483c4a4994f
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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