Hydrochloric Acid → HCID 178524759, compound

HRID 2267087Notes

Reaction equation

HRID 2267087 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[C:9]([O:10]C(=O)C)=[C:8]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]([CH2:22][O:23]C(=O)C)=[N:6][CH:5]=1.[OH-].[Na+].C(OCC)C.Cl>CO>[CH2:15]([O:14][C:8]1[C:7]([CH2:22][OH:23])=[N:6][CH:5]=[C:4]([C:9]=1[OH:10])[C:3]([OH:27])=[O:2])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 59600561Methyl 4-acetoxy-6-(acetoxymethyl)-5-(benzyloxy)nicotinate

Product 1

HCID 178524759HCID 178524759, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound 8 (46.8 g, 125 mmol) in methanol (140 ml) was added a 2N aqueous sodium hydroxide solution (376 ml) under ice-cooling, and this was stirred at 50° C. for 40 minutes. To the reaction solution were added diethyl ether and 2N hydrochloric acid under ice-cooling, and precipitated crystals were filtered. Resulting crystals were washed with water and diethyl ether to obtain 5-benzyloxy-4-hydroxy-6-hydroxymethyl-nicotinic acid 9 (23.3 g, 68%) as a colorless crystal.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. customResulting crystals
  6. washwere washed with water and diethyl ether

Sources & evidence

ORD record
ord-23808af2a3464063968c36f931cba5dc
Source dataset
uspto-grants-2010_12
Patent number
US07858788B2

Reaction notes

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