Diethyl Ether → HCID 21391826, compound

HRID 461657Notes

Reaction equation

HRID 461657 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[NH:12][NH2:13].CCOCC>C1(O)C=CC=CC=1>[ClH:1].[N+:8]([C:7]1[C:2]([NH:13][NH:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 21391826HCID 21391826, compound

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Procedure

A 24 g (0.15 mole) portion of 2-chloro-3-nitropyridine in 153 ml of phenol at 45°-50° was treated portionwise with 20.5 g (0.20 mole) of ethyl carbazate, keeping the temperature below 60°, using rapid mechanical stirring. The reaction mixture was heated on a steam bath for 5 hr, cooled to 45 -55°, and poured into 750 ml of anhydrous ether, using rapid hand stirring. A light orange solid was collected, washing with 400 ml of anhydrous ether, m.p. 142°-152° dec. Yield: 34 g (85%).

Workup

  1. customthe temperature below 60°
  2. temperatureThe reaction mixture was heated on a steam bath for 5 hr
  3. temperaturecooled to 45 -55°
  4. customA light orange solid was collected
  5. washwashing with 400 ml of anhydrous ether, m.p. 142°-152° dec

Sources & evidence

ORD record
ord-b63abd60343b4b5a8b743a31e00d4620
Source dataset
uspto-grants-1977_12
Patent number
US04064134

Reaction notes

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