Hydrochloric Acid → 2-Methoxymethyl-thiazolo[5,4-b]pyridin-6-yl-carboxylic acid

HRID 2288475Notes

Reaction equation

HRID 2288475 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15]C)=[O:14])=[CH:8][N:7]=2.[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([OH:15])=[O:14])=[CH:8][N:7]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18412416Methyl 2-methoxymethyl-thiazolo[5,4-b]pyridine-6-carboxylate

Product 1

HCID 184124392-Methoxymethyl-thiazolo[5,4-b]pyridin-6-yl-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.1 g (4.62 mMol) of methyl 2-methoxymethyl-thiazolo[5,4-b]pyridine-6-carboxylate and 9.2 ml of 2N sodium hydroxide solution were stirred into 50 ml of ethanol for one hour at room temperature. Then 9.2 ml of 2N hydrochloric acid were added, the alcohol was distilled off, and it was diluted with 20 ml of water. The aqueous phase was acidified with concentrated hydrochloric acid whilst cooling with ice, the beige precipitate formed was filtered off, then washed with water and dried. Yield: 1.03 g (100% of theory), Rf value: 0.10 (silica gel; ethyl acetate/petroleum ether=3:7)

Workup

  1. distillationthe alcohol was distilled off
  2. additionit was diluted with 20 ml of water
  3. temperaturewhilst cooling with ice
  4. customthe beige precipitate formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-c70073e9fe7f4a0c9c711fbceb52f7cd
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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