Hydrogen Bromide → HCID 21561613, compound

HRID 1581133Notes

Reaction equation

HRID 1581133 reaction equation
COC([O:5][C:6]1[C:7]([CH3:18])=[N:8][CH:9]=[C:10]([CH2:12][O:13][C:14]([O:16][CH3:17])=[O:15])[CH:11]=1)=O.Br.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:17][O:16][C:14]([O:13][CH2:12][C:10]1[CH:11]=[C:6]([OH:5])[C:7]([CH3:18])=[N:8][CH:9]=1)=[O:15]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 21561588HCID 21561588, compound

Product 1

HCID 21561613HCID 21561613, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1 g. of 3-methoxycarbonyloxy-5-methoxycarbonyloxymethyl-2-methylpyridine in an aqueous ethanol (10 ml. of ethanol and 5 ml. of water) was adjusted to pH 1-1.5 with 10% hydrobromic acid. The mixture was heated at 90°C for 30 minutes, then cooled and neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated into a small volume and the addition of n-hexane gave 0.45 g. of the desired product as colorless crystals melting at 187°-189°C, which showed no depression of melting point on admixture with the authentic sample and the IR spectrum coincided with that of the standard completely.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated into a small volume
  5. additionthe addition of n-hexane
  6. customgave 0.45 g

Sources & evidence

ORD record
ord-dd239861ed674cd599bc466206cc2840
Source dataset
uspto-grants-1976_01
Patent number
US03935311

Reaction notes

Loading…