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Acetic Acid → Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamate

HRID 637757
Notes
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Reaction equation

HRID 637757 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.[C:15]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[C:16]([C:15]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][C:6]1[CH:9]=[CH:10][C:3]([N:2]([CH3:14])[CH3:1])=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 2913524-Dimethylamino-2-nitrobenzaldehyde

Product 1

HCID 14365894Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamateYield 61.8%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

A mixture of 8.9 grams (g) [50 millimoles (mmol)] of 4-dimethylamino-2-nitrobenzaldehyde [H. Baumann et al, German Pat. 2,363,458], 23.7 g (148 mmol) of diethyl malonate, 3.44 g (40.4 mmol) of piperidine and 2.43 g (40.4 mmol) of acetic acid in 400 milliliters (mL) of toluene was refluxed for 16 hours under argon with a Dean Stark trap attached. The solution was cooled to room temperature and washed with 200 mL of 5% aqueous potassium hydroxide (KOH). The organic phase was separated, dried over sodium sulfate (Na2SO4), filtered, and the solvent evaporated. The dark red solid residue was dissolved in 40 mL of methylene chloride (CH2Cl2) and 100 mL of hexane added. After standing for one hour, the solution was filtered to yield 10.4 g of orange crystals. Recrystallization from CH2Cl2 -hexane produced an analytical sample, m.p. 101°-102° C.

Workup

  1. temperaturewas refluxed for 16 hours under argon with a Dean Stark trap
  2. washwashed with 200 mL of 5% aqueous potassium hydroxide (KOH)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. dissolutionThe dark red solid residue was dissolved in 40 mL of methylene chloride (CH2Cl2)
  8. addition100 mL of hexane added
  9. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-2fd745098fa14c2894c5f27cc2299328
Source dataset
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04558130

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes