Water → HCID 53642745, compound

HRID 2119133Notes

Reaction equation

HRID 2119133 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[OH-].[Na+].[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)=[O:13].O>CN(C=O)C>[C:22]1([CH2:21][O:20][C:17]2[CH:16]=[CH:15][C:14]([C:12](=[O:13])[CH:11]=[CH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:19][CH:18]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Product 1

HCID 53642745HCID 53642745, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A sample of a 42.4 g (0.4 mole) of pyridine-2-carboxaldehyde was added to a solution of 83.6 mL of 10% sodium hydroxide and 100 mL of DMF at 10° C. Then a solution of 47.2 g (0.21 mole) of 4-benzyloxyacetophenone in 300 mL of DMF was added slowly over a period of 1 hr to the mixture keeping the temperature of the reaction mixture at 5°-13° C. After 1.5 hr, the reaction mixture was allowed to warm to room temperature. Water was added, and the product precipitated out as a solid. The solid was crystallized from 95% ethanol to give 48.2 g (73% yield) of the title compound as a yellow solid, mp=131°-134° C. An additional 3.3 g (5% yield) of the product was obtained from the mother liquor, mp=131°-134° C.

Workup

  1. customat 5°-13° C
  2. customthe product precipitated out as a solid
  3. customThe solid was crystallized from 95% ethanol

Sources & evidence

ORD record
ord-37677ce0b33f456980b779fc686e5502
Source dataset
uspto-grants-1987_07
Patent number
US04683239

Reaction notes

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