Hydrochloric Acid → 5-(3-Hydroxypropyl)-1-{[4-(methyloxy)phenyl]methyl}-1,2-dihydro-3,6-pyridazinedione

HRID 656951Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:15](=[O:16])[C:14]([CH2:17][CH2:18][C:19](OCCCC)=[O:20])=[CH:13][C:12](=[O:26])[NH:11]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[OH:20][CH2:19][CH2:18][CH2:17][C:14]1[C:15](=[O:16])[N:10]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[NH:11][C:12](=[O:26])[CH:13]=1

Participants

Conditions

Temperature: -30 °C

Procedure

Butyl 3-(2-{[4-(methyloxy)phenyl]methyl}-3,6-dioxo-1,2,3,6-tetrahydro-4-pyridazinyl)propanoate (0.56 g, 1.56 mmol) was dissolved in dry THF (30 ml). The solution under argon was cooled to −30° C., treated dropwise with a 1M solution of lithium aluminium hydride in THF (1.8 ml, 1.8 mmol), allowed to warn gradually to 0° C. and stirred in an ice bath for 30 minutes. 2M Hydrochloric acid was added until pH 3 was obtained, and the mixture was partitioned between water and ethyl acetate. The aqueous was re-extracted with ethyl acetate and the combined organic solution dried and evaporated. Chromatography of the residue on silica, eluting with ethyl acetate, gave the product as a white solid (300 mg, 67%).

Workup

customto warn gradually to 0° C.
customwas obtained
customthe mixture was partitioned between water and ethyl acetate
extractionThe aqueous was re-extracted with ethyl acetate
customthe combined organic solution dried
customevaporated
washChromatography of the residue on silica, eluting with ethyl acetate

Sources & evidence

ORD record: ord-aebe7b2b1ad248d8abad18a65e19c29a
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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