Water → HCID 86717327, compound

HRID 588635Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[O:22])[CH:16]=1.[Li+].CC([N-]C(C)C)C.O>C1COCC1.C(OCC)(=O)C>[Cl:8][C:6]1[N:5]=[N:4][C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:2]([Cl:1])[C:7]=1[CH:21]([C:17]1[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=1)[OH:22]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4,6-dichloro-3-phenyl-pyridazine (2.27 g, 0.01 mol) in dry THF (30 mL) was added pyridine-3-carbaldehyde (1.3 g, 0.012 mol). The reaction mixture was cooled down to −78° C. and a solution of LDA (2 N, 22 mL) was added dropwise, keeping the internal temperature below −50° C. The reaction mixture was stirred for 3 h, then water and ethyl acetate were added. Phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried (phase separator cartridge) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 9:1 to 8:2) yielding the title compound as a solid (4.1 g).

Workup

customthe internal temperature below −50° C
customPhases were separated
extractionthe aqueous phase was extracted with ethyl acetate
customThe combined organic phases were dried (phase separator cartridge)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (silica gel, isohexane/ethyl acetate 9:1 to 8:2)

Sources & evidence

ORD record: ord-5a0615ea84e347349d0ac9fe810c68f5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227976B2

Reaction notes

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