Ethyl bromoacetate → 6-(4-carbethoxymethoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

HRID 2371921Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[C:23]([CH2:22][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)([O:25][CH2:26][CH3:27])=[O:24]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.00 g (10.5 mmol) of the phenol prepared above, 1.60 g (11.6 mmol) of anhydrous K2CO3, 1.304 ml (11.8 mmol) of ethyl bromoacetate, and 40 ml of DMF is heated at 100° C. for 2 hrs under N2. The DMF is removed under vacuum and the residue taken up in 150 ml of EtOAc and 75 ml of water. The organic phase is washed with 50 ml of 5% aqueous NaOH, twice with saturated NaCl, dried (MgSO4), filtered, and the solvent removed to leave 2.186 g of a slightly yellow solid. This is recrystallized from hexane-EtOAc to give 2.01 g of 6-(4-carboethoxymethoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone as a white, crystalline solid, m.p. 127°-129° C. Yield 69%.

Workup

customThe DMF is removed under vacuum
washThe organic phase is washed with 50 ml of 5% aqueous NaOH, twice with saturated NaCl
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent removed
customto leave 2.186 g of a slightly yellow solid
customThis is recrystallized from hexane-EtOAc

Sources & evidence

ORD record: ord-a2f476b1e41a4c12965cdb2878e5fb56
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05096904

Reaction notes

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