2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → HCID 56932249, compound

HRID 982004Notes

Reaction equation

HRID 982004 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[CH:7]=[C:8]([C:15]([CH3:17])=O)[C:9]([O:11][CH2:12][CH2:13][Br:14])=[O:10])([O-:3])=[O:2].[NH2:21]/[C:22](/[CH3:29])=[CH:23]\[C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCCC1>[CH3:29][C:22]1[NH:21][C:15]([CH3:17])=[C:8]([C:9]([O:11][CH2:12][CH2:13][Br:14])=[O:10])[CH:7]([C:6]2[CH:18]=[CH:19][CH:20]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 54359700HCID 54359700, compound

Product 1

HCID 56932249HCID 56932249, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

58.8 g of 2-bromoethyl 2-(3-nitrobenzylidene)-acetoacetate and 22.5 g of ethyl 3-aminocrotonate in 250 ml of tetrahydrofuran are heated at the boil for 3 h. The mixture is stirred for 8 h at room temperature, after which the solvent is distilled off in vacuo and the solid residue is dissolved in hot 2-propanol. The title compound crystallises out on cooling. It is filtered off under suction, washed with cold 2-propanol and dried. 65 g of product of m.p. 158°-159° C. are obtained.

Workup

  1. distillationafter which the solvent is distilled off in vacuo
  2. dissolutionthe solid residue is dissolved in hot 2-propanol
  3. customThe title compound crystallises out
  4. temperatureon cooling
  5. filtrationIt is filtered off under suction
  6. washwashed with cold 2-propanol
  7. customdried

Sources & evidence

ORD record
ord-df2f6428edd54d1ba8a713bbe8552ff5
Source dataset
uspto-grants-1991_02
Patent number
US04994461

Reaction notes

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