p-Aminoacetophenone → HCID 38567, compound

HRID 848162Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].OCC(C1C=CC=CC=1)=O.[N:21]1[CH:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][CH:22]=1.[OH-].[Na+]>>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH:1]=[CH:27][C:24]2[CH:25]=[CH:26][N:21]=[CH:22][CH:23]=2)=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 7468p-Aminoacetophenone

HCID 133894-Pyridinecarboxaldehyde

HCID 14798Sodium Hydroxide

HCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 38567HCID 38567, compoundYield 98.2%

Procedure

The procedure is as in Example 11, starting from 1.35 g of 4-aminoacetophenone (instead of 24 g of 2-hydroxyacetophenone) and 2.14 g of pyridine-4-carbaldehyde instead of 21 g and using a 2.5 N aqueous sodium hydroxide solution instead of an 11 N solution. 2.2 g of 1-(4-aminophenyl) 3-(4-pyridyl) 2-propene-1-one which melts at 207° C. are obtained.

Sources & evidence

ORD record: ord-a315b919ea1b402d809a395226a32c98
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04294841

Reaction notes

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