Ethylenediamine → 6-[4-[2-aminoethylcarbamoylmethoxy]phenyl]-4,5-dihydro3(2H)-pyridazinone

HRID 344645Notes

Reaction equation

HRID 344645 reaction equation
[C:1]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH2:15][CH2:16][C:17](=[O:20])[NH:18][N:19]=2)=[CH:10][CH:9]=1)([O:3]CC)=O.[CH2:21]([NH2:24])[CH2:22][NH2:23]>>[NH2:23][CH2:22][CH2:21][NH:24][C:1]([CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH2:15][CH2:16][C:17](=[O:20])[NH:18][N:19]=2)=[CH:12][CH:13]=1)=[O:3]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 136876766-(4-carbethoxymethoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 150163426-[4-[2-aminoethylcarbamoylmethoxy]phenyl]-4,5-dihydro3(2H)-pyridazinoneYield 80.3%

Conditions

Temperature
60 °C

Procedure

A mixture of 2.85 g (10.3 mmol) of 6-(4-carbethoxymethoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (prepared as described in Example 13) and 9.3 g (155 mmol) of ethylenediamine is heated at 60° C. under N2 for 30 min. Volatile materials are removed in vacuo, and the residue is recrystallized from methanol-EtOAc to give 2.40 g of 6-[4-[2-aminoethylcarbamoylmethoxy]phenyl]-4,5-dihydro3(2H)-pyridazinone as a white solid, m.p. 176°-177.5° C. Yield, 80%.

Workup

  1. customVolatile materials are removed in vacuo
  2. customthe residue is recrystallized from methanol-EtOAc

Sources & evidence

ORD record
ord-af1e8bb45c7c4471a582f7e2fe81d92f
Source dataset
uspto-grants-1991_10
Patent number
US05053338

Reaction notes

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