(4-Nitrophenyl)acetic acid → HCID 15051083, compound

HRID 1089394Notes

Reaction equation

HRID 1089394 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1C=O.N1CCCCC1.CC(N(C)C)=O>O>[OH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:24](/[CH:11]=[CH:10]/[C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[CH:23][CH:20]=1

Participants

6

Reactant 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 8082PiperidineHCID 31374DimethylacetamideHCID 13167400HCID 13167400, compound

Product 1

HCID 15051083HCID 15051083, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-Nitrophenylacetic acid (131.4 g, 0.73 mole), -(3-hydroxypropyloxy)benzaldehyde (130.8 g, 0.73 mole, prepared as in U.S. Patent 2,824,084), piperidine (14.2 g, 0.17 mole) and dimethylacetamide were placed in a 1 L round-bottom flask fitted with a mechanical stirrer, a condenser and a thermometer connected to a controller and a heating mantle. The resulting mixture was stirred and warmed to 80° C., at which temperature a brisk evolution of gas was induced. Stirring was continued at 80° C. for 18 h. The mixture was then poured into a beaker and stirred and diluted to 3 L with ice and water. The solid that appeared was collected by filtration, washed with water and dried to give a deep yellow product (142 g). Two crystallizations from aqueous ethanol afforded the analytical sample (76.9 g, 35%).

Workup

  1. customfitted with a mechanical stirrer, a condenser
  2. stirringStirring
  3. additionThe mixture was then poured into a beaker
  4. stirringstirred
  5. filtrationThe solid that appeared was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-a70a9c5c15534fdd9e51a0c167eb7455
Source dataset
uspto-grants-1990_10
Patent number
US04966730

Reaction notes

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