Pyridine → HCID 21493313, compound

HRID 1973231Notes

Reaction equation

HRID 1973231 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([O:11][CH2:12][CH3:13])[N:3]=1.N1C=CC=CC=1.[Cl:20][CH2:21][C:22](Cl)=[O:23]>CCOCC>[N+:8]([C:6]1[CH:5]=[C:4]([O:11][CH2:12][CH3:13])[N:3]=[C:2]([NH:1][C:22](=[O:23])[CH2:21][Cl:20])[CH:7]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 21493349HCID 21493349, compound

Product 1

HCID 21493313HCID 21493313, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-amino-4-nitro-6-ethoxypyridine (29.4 grams) in absolute ether (150 ml), and pyridine (25 grams) are charged into a glass reaction vessel equipped with stirrer, thermometer and addition funnel. The mixture is cooled to a temperature of about 0° C and chloroacetyl chloride (11.3 grams) dissolved in ether (50 ml) is then slowly added thereto with stirring over a period of about 20 minutes. Stirring and cooling are continued for an additional period of about 30 minutes. The resulting precipitate is then recovered from the reaction medium by filtration, is washed first with aqueous sodium carbonate and then with water, and is dried to yield the desired product N-(4-nitro-6-ethoxy-2-pyridyl)-α-chloroacetamide.

Workup

  1. customequipped with stirrer
  2. additionthermometer and addition funnel
  3. additionis then slowly added
  4. stirringStirring
  5. temperaturecooling
  6. waitare continued for an additional period of about 30 minutes
  7. filtrationThe resulting precipitate is then recovered from the reaction medium by filtration
  8. washis washed first with aqueous sodium carbonate
  9. dry with materialwith water, and is dried

Sources & evidence

ORD record
ord-7e55d5395a6a4086bca5ba1ce253165a
Source dataset
uspto-grants-1976_12
Patent number
US03996352

Reaction notes

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