(4-Nitrophenyl)acetic acid → 4'-Diethylamino-4-nitrostilbene

HRID 476809

Reaction equation

HRID 476809 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23]C(O)=O)=[CH:19][CH:18]=1)([O-:16])=[O:15].N1CCCCC1>O>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:23][C:20]2[CH:21]=[CH:22][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 8082PiperidineHCID 671144-(Diethylamino)benzaldehyde

Product 1

HCID 6246574'-Diethylamino-4-nitrostilbene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5.00 g (28 mmol) of 4-diethylaminobenzaldehyde, 5.62 g (31 mmol) of 4-nitrophenylacetic acid, 2.40 g (28 mmol) of piperidine, and 100 mL of xylenes was heated with stirring at reflux for 20 hours with continuous removal of water using a Dean-Stark apparatus. The mixture turned dark red. Approximately half the xylenes was distilled, and the residue was cooled to 3 0° C. Red crystals separated which were collected and then recrystallized from isopropanol/pyridine. Yield: 4.05 g (48%), mp 179-181 (lit2 182°-182.5° C.).

Workup

  1. temperaturewas heated
  2. distillationApproximately half the xylenes was distilled
  3. customRed crystals separated which
  4. customwere collected
  5. customrecrystallized from isopropanol/pyridine
  6. customYield: 4.05 g (48%), mp 179-181 (lit2 182°-182.5° C.)

Sources & evidence

ORD record
ord-80647dae8203445495a8ed0ef8b2870e
Source dataset
uspto-grants-1989_12
Patent number
US04886339

Linked notes

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