Ammonium Chloride → HCID 178498811, compound

HRID 2267100Notes

Reaction equation

HRID 2267100 reaction equation
[CH3:1][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.[Cl-].[NH4+]>CO>[CH3:1][O:2][C:3](=[O:27])[C:4]1[C:9]([OH:10])=[C:8]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:7]([CH2:22][OH:23])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 59600561Methyl 4-acetoxy-6-(acetoxymethyl)-5-(benzyloxy)nicotinate

Product 1

HCID 178498811HCID 178498811, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound 8 (9.5 g, 25.4 mmol) was dissolved in methanol (50 ml), and a sodium methylate methanol solution (7.35 ml, 38.1 mmol) was added. The solution was stirred at room temperature for 1 hour, an aqueous saturated ammonium chloride solution was added, and crystals were collected by filtration. Washing with water and diethyl ether afforded 5-benzyloxy-4-hydroxy-6-hydroxymethyl-nicotinic acid methyl ester 18 (4.68 g, 64%) as a colorless crystal.

Workup

  1. filtrationcrystals were collected by filtration
  2. washWashing with water and diethyl ether

Sources & evidence

ORD record
ord-407f046e9bd04256bb5adfb9bf185c6f
Source dataset
uspto-grants-2010_12
Patent number
US07858788B2

Reaction notes

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