Ethanol → 2-(5-Bromopyrid-2-ylamino)-1-ethoxycarbonyl-1-nitroethene

HRID 542885Notes

Reaction equation

HRID 542885 reaction equation
C(O[CH:4]=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N+:6]([O-:8])=[O:7])C.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1.C(O)C>C1(C)C=CC=CC=1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][CH:4]=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N+:6]([O-:8])=[O:7])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 706222-Amino-5-bromopyridineHCID 54104329Ethyl 3-ethoxy-2-nitroprop-2-enoate

Product 1

HCID 867414302-(5-Bromopyrid-2-ylamino)-1-ethoxycarbonyl-1-nitroetheneYield 63.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-ethoxy-1-ethoxycarbonyl-1-nitroethene (5.7 g) and 2-amino-5-bromopyridine (5.2 g) in toluene was heated at reflux with slow removal of the ethanol formed during 2 hours. The reaction mixture was cooled and concentrated in vacuo to give a yellow powder which was triturated with hot ethanol, to give 2-(5-bromopyrid-2-ylamino)-1-ethoxycarbonyl-1-nitroethene (6.0 g) in the form of a pale yellow powder, m.p. 141°-142° C.

Workup

  1. temperaturewas heated
  2. customformed during 2 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customto give a yellow powder which
  6. customwas triturated with hot ethanol

Sources & evidence

ORD record
ord-c3a8d47b0aba487a8228d03f5c3e5321
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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