2-Nitrobenzaldehyde → HCID 14676007, compound

HRID 2351950Notes

Reaction equation

HRID 2351950 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:17])[CH2:13][C:14]([CH3:16])=O.[CH:25]([NH:28][C:29](=[O:34])/[CH:30]=[C:31](\[NH2:33])/[CH3:32])([CH3:27])[CH3:26]>C(O)C>[CH3:32][C:31]1[NH:33][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:17])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:30]=1[C:29]([NH:28][CH:25]([CH3:27])[CH3:26])=[O:34]

Participants

5

Reactant 3

HCID 111012-NitrobenzaldehydeHCID 83577Hexyl acetoacetateHCID 55280984HCID 55280984, compound

Product 1

HCID 14676007HCID 14676007, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

o-Nitrobenzaldehyde (3.8 g, 0.025 mole), n-hexyl acetoacetate (4.6 g, 0.025 mole) and 3-aminocrotonic isopropylamide (3.5 g, 0.025 mole) are dissolved in ethanol (50 ml), and the mixture is refluxed for 8 hours. After the reaction, the solvent is distilled off under reduced pressure. The residue is dissolved in elution solvent [chloroform:carbon tetrachloride:ethyl formate:formic acid:ethanol (10:10:8:1:2)] (30 ml) and subjected to column chromatography [silica gel 60 Art. 9385 (Manufactured by Merck Co.), 300 g, φ40 mm×50 cm]. The fraction containing the desired compound is regulated to pH 10 with 28% aqueous ammonia, and the organic layer is separated, washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue is recrystallized from 80% ethanol to give the title compound (3.31 g, yield 29.9%) as yellow prisms, m.p. 175°-178° C.

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. customAfter the reaction
  3. distillationthe solvent is distilled off under reduced pressure
  4. dissolutionThe residue is dissolved in elution solvent [chloroform:carbon tetrachloride:ethyl formate:formic acid:ethanol (10:10:8:1:2)] (30 ml)
  5. additionThe fraction containing the desired compound
  6. customthe organic layer is separated
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is recrystallized from 80% ethanol

Sources & evidence

ORD record
ord-4eb28a0b4db041c19ac219c75ab11861
Source dataset
uspto-grants-1989_10
Patent number
US04874773

Reaction notes

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