Diketene → Acetoacetic acid N-[4-(6-oxo-1,4,5,6-tetrahydropyridazin-3yl)-phenyl]-amide

HRID 247366

Reaction equation

HRID 247366 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][C:11](=[O:14])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:15]=[C:16]1[O:20][C:18](=[O:19])[CH2:17]1>CN(C)C=O>[O:14]=[C:11]1[NH:10][N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:18](=[O:19])[CH2:17][C:16]([CH3:15])=[O:20])=[CH:7][CH:6]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 13646979Acetoacetic acid N-[4-(6-oxo-1,4,5,6-tetrahydropyridazin-3yl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 g (0.106 mole) of 3-(4-aminophenyl)-6-oxo-1,4,5,6-tetrahydropyridazine in 250 ml of dimethylformamide are stirred with 9.47 g (0.113 moles) of diketene for 12 hours at room temperature. After the mixture has been concentrated, the residue is boiled up with 100 ml of ethanol, and the product is filtered off after cooling.

Workup

  1. concentrationAfter the mixture has been concentrated
  2. filtrationthe product is filtered off
  3. temperatureafter cooling

Sources & evidence

ORD record
ord-06341a1303b7490f95e684614b1007ea
Source dataset
uspto-grants-1987_11
Patent number
US04707479

Linked notes

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