Sodium Hydroxide → HCID 59129740, compound

HRID 1991460Notes

Reaction equation

HRID 1991460 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:15])=[C:9]([CH2:13][CH3:14])[C:10]=2[CH3:12])[S:5][C:4]=1[C:16]([O:18]C)=[O:17])#[N:2].[OH-].[Na+]>C(O)C>[C:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:15])=[C:9]([CH2:13][CH3:14])[C:10]=2[CH3:12])[S:5][C:4]=1[C:16]([OH:18])=[O:17])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59129744HCID 59129744, compound

Product 1

HCID 59129740HCID 59129740, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-cyano-5-ethyl-4,6-dimethylthieno[2,3-b]pyridine-2-carboxylate (2.70 g, 9.9 mmol), prepared above, in ethanol (100 mL), was added aqueous NaOH (1.25 N, 15.7 mL, 19.6 mmol), and the mixture was stirred for 2 h at 60° C. The volatiles were removed under reduced pressure and the residue was dissolved in water (150 mL) and then acidified using concentrated HCl until the pH was adjusted to 5-6. The precipitate was collected via filtration and washed thoroughly with water, dried in air to give 3-cyano-5-ethyl-4,6-dimethylthieno[2,3-b]pyridine-2-carboxylic acid (2.38 g, 93%). MS (ES−) m/z: 259.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in water (150 mL)
  3. filtrationThe precipitate was collected via filtration
  4. washwashed thoroughly with water
  5. customdried in air

Sources & evidence

ORD record
ord-31312382c1374ac4825b84e9e067c9d9
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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