Ethanol → Ethyl (3-oxo-2,3,4,5-Tetrahydropyridazin-6-yl)propionate

HRID 987905Notes

Reaction equation

[OH2:1].[NH2:2][NH2:3].O=[C:5]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:6][CH2:7]C(OCC)=O.[CH2:20](O)C>>[O:1]=[C:7]1[CH2:6][CH2:5][C:13]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:3][NH:2]1

Participants

Reactant 3

HCID 702Ethanol

HCID 24654Hydrazine hydrate (1:1)

HCID 80592Diethyl 4-oxoheptanedioate

Product 1

HCID 86759212Ethyl (3-oxo-2,3,4,5-Tetrahydropyridazin-6-yl)propionate

Procedure

To a solution of hydrazine monohydrate (95 mmol, 4.76 g) in abs. ethanol (50 mL) was added diethyl 4-oxopimelate (100 mmol, 23.03 g). The mixture was stirred at rt. for 1 h and evaporated to dryness in vacuo to give the desired product (18.96 g, quantitative) as a pure (HPCL 260 nm) white solid. The material was analyzed by HPLC (260 nm) and found to be pure. UV λmax 242 nm. 1H NMR (CDCl3): δ 8.61 (s br, 1H, NH), 4.11 (q, J=7.1 Hz, 2H, CH2), 2.60-2.55 (m, 4H, 2CH2), 2.50.2.40 (m, 4H, 2CH2), 1.22 (t, J=7.1 Hz, 3H, CH3). 13C NMR (CDCl3): δ 172.41, 167.16, 153.35, 60.36, 30.85 29.76, 25.17, 14.00. FAB+ MS: 199.1085 (M+H+, calc. for C9H14N2O3+H+ 199.1083).

Workup

customevaporated to dryness in vacuo

Sources & evidence

ORD record: ord-dd865cb172e44ad4bf25a80d10ee4449
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632919B1

Reaction notes

Loading…