Ethyl Acetoacetate → HCID 69285281, compound

HRID 2121644Notes

Reaction equation

HRID 2121644 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=O>C1CCCCC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:19]([O:18][C:12](=[O:17])[CH:13]=[C:14]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[CH3:16])[CH3:20]

Participants

5

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 69285281HCID 69285281, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8079CyclohexeneSolvent

Procedure

20 g (156 mmol) of 4-fluor-3-nitro-aniline, 18.9 ml (134 mmol) of ethyl acetoacetate in cyclohexene (35 ml) were treated with p-toluene sulfonic acid monohydrate (0.24 g) and heated for 9 h at reflux under a water separator funnel. The solvent was removed in vacuo, the residue applied to silica gel column with AcOEt/n-hexane (1:1)) as eluent. Combination of the purified fractions and concentration in vacuo gave 4.3 g (12.5%) of the 3-(4-fluoro-3-nitro-phenylamino)-but-2-enoic acid ethyl ester as yellow crystals. ISN mass spectrum, m/e: 267.2 (M−1 calculated for C12H13FN2O4: 267).

Workup

  1. temperatureheated for 9 h
  2. temperatureat reflux under a water separator funnel
  3. customThe solvent was removed in vacuo
  4. concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-676adaa960d149ab87e863676cace9f0
Source dataset
uspto-grants-2004_02
Patent number
US06696467B2

Reaction notes

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