Ethylenediamine → 6-{4-[2-aminoethylcarbamoylpropyloxy]-3-chlorophenyl}-4,5-dihydro-3(2H)-pyridazinone

HRID 344646Notes

Reaction equation

HRID 344646 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:12][C:11]=1[Cl:23])([O:3]CC)=O.[CH2:24]([NH2:27])[CH2:25][NH2:26]>>[NH2:26][CH2:25][CH2:24][NH:27][C:1]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:12][C:11]=1[Cl:23])=[O:3]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 136876936-[4-carboethoxypropyloxy-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 150163626-{4-[2-aminoethylcarbamoylpropyloxy]-3-chlorophenyl}-4,5-dihydro-3(2H)-pyridazinone

Procedure

A solution of 4.5 g (13.3 mol) of 6-[4-carboethoxypropyloxy-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone (prepared as described in Example 23) in 12.0 g 199 mmol) of ethylenediamine is heated at 95° C. under N2 for 12 hrs. Volatiles are removed under vacuum and the residue recrystallized from EtOAc-methanol to give 3.65 g of 6-{4-[2-aminoethylcarbamoylpropyloxy]-3-chlorophenyl}-4,5-dihydro-3(2H)-pyridazinone as a white powder. Yield, 78%.

Workup

  1. customVolatiles are removed under vacuum
  2. customthe residue recrystallized from EtOAc-methanol

Sources & evidence

ORD record
ord-0127ef3f13c84b7fa5d4033587ffe851
Source dataset
uspto-grants-1991_10
Patent number
US05053338

Reaction notes

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