Sodium Hydroxide → HCID 21891739, compound

HRID 720679Notes

Reaction equation

HRID 720679 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:13])[CH3:12])=[CH:8][S:7][C:6]=1[CH3:14])=[O:4].[OH-].[Na+]>CO>[C:11]([NH:10][C:9]1[C:5]([C:3]([OH:4])=[O:2])=[C:6]([CH3:14])[S:7][CH:8]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2808345Methyl 4-(acetylamino)-2-methyl-3-thiophenecarboxylate

Product 1

HCID 21891739HCID 21891739, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-acetylamino-2-methyl-thiophene-3-carboxylic acid methyl ester (250 mg, 1.17 mmol) in methanol (4.0 mL) at 25° C. was treated with a 1N aqueous sodium hydroxide solution (3.5 mL, 3.51 mmol). The reaction was stirred at 25° C. for 28 h. At this time, the reaction was concentrated in vacuo, diluted with water (15 mL), and then acidified to pH=2 by the addition of a 1N aqueous hydrochloric acid solution. The resulting slurry was cooled to 0° C. The solid was collected by filtration, washed with water, and the dried in vacuo to afford 4-acetylamino-2-methyl-thiophene-3-carboxylic acid (212 mg, 90.9%) as a tan solid: LR-MS for C8H9NO3 (M−H)+ at m/z=198.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. additiondiluted with water (15 mL)
  3. additionacidified to pH=2 by the addition of a 1N aqueous hydrochloric acid solution
  4. temperatureThe resulting slurry was cooled to 0° C
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customthe dried in vacuo

Sources & evidence

ORD record
ord-ee24076b81a64bdb8205628db97f9b09
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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