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

HRID 637757

反応式

HRID 637757 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 14365894Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamate収率 61.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2fd745098fa14c2894c5f27cc2299328
出典データセット
uspto-grants-1985_12
特許番号
US04558130

関連ノート

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