(4-Nitrophenyl)acetic acid → HCID 54267513, compound

HRID 476810Notes

Reaction equation

HRID 476810 reaction equation
[CH2:1]([N:5]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27]C(O)=O)=[CH:23][CH:22]=1)([O-:20])=[O:19].N1CCCCC1>O>[CH2:1]([N:5]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH:27][C:24]2[CH:25]=[CH:26][C:21]([N+:18]([O-:20])=[O:19])=[CH:22][CH:23]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 8082PiperidineHCID 6053914-(Dibutylamino)benzaldehyde

Product 1

HCID 54267513HCID 54267513, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-30 °C

Procedure

A mixture of 5.00 g (21 mmol) of 4-dibutylaminobenzaldehyde, 4.27 g (24 mmol) of 4-nitrophenylacetic acid, 1.80 g (21 mmol) of piperidine, and 50 mL of xylenes was heated with stirring at reflux of 20 hours with continuous removal of water using a Dean-Stark apparatus. The mixture turned dark red. Approximately half the xylenes was distilled, 20 mL of heptane was added, and the residue was cooled to -30° C. Red crystals separated which were collected and then recrystallized from toluene/heptane. Yield: 2.81 g (37%), mp 117-119 (lit2 182°-182.5° C.).

Workup

  1. temperaturewas heated
  2. distillationApproximately half the xylenes was distilled
  3. addition20 mL of heptane was added
  4. customRed crystals separated which
  5. customwere collected
  6. customrecrystallized from toluene/heptane
  7. customYield: 2.81 g (37%), mp 117-119 (lit2 182°-182.5° C.)

Sources & evidence

ORD record
ord-22a2e76f59b548a28fcd5be87fe4cc7b
Source dataset
uspto-grants-1989_12
Patent number
US04886339

Reaction notes

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