Hydrochloric Acid → HCID 67527302, compound

HRID 656954Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:15](=[O:16])[CH:14]=[C:13]([CH2:17][CH2:18][C:19](OCCCC)=[O:20])[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:13]1[C:12](=[O:26])[NH:11][N:10]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:15](=[O:16])[CH:14]=1

Participants

Conditions

Temperature: -30 °C

Procedure

Butyl 3-(1-{[4-(methyloxy)phenyl]methyl}-3,6-dioxo-1,2,3,6-tetrahydro-4-pyridazinyl)propanoate (0.43 g, 1.19 mmol) was dissolved in dry THF (20 ml). The solution under argon was cooled to −30° C., treated dropwise with a 1M solution of lithium aluminium hydride in THF (1.4 ml, 1.4 mmol), allowed to warm gradually to 0° C. and stirred in an ice bath for 30 minutes. 2M hydrochloric acid was added until the pH was 3 and the mixture was partitioned between water and ethyl acetate. The aqueous phase was re-extracted with ethyl acetate and the combined organic solution dried and evaporated. The resulting solid was triturated under ethyl acetate, filtered off, washed with ethyl acetate and dried under vacuum to give the product (241 mg, 70%).

Workup

temperatureto warm gradually to 0° C.
customthe mixture was partitioned between water and ethyl acetate
extractionThe aqueous phase was re-extracted with ethyl acetate
customthe combined organic solution dried
customevaporated
customThe resulting solid was triturated under ethyl acetate
filtrationfiltered off
washwashed with ethyl acetate
customdried under vacuum

Sources & evidence

ORD record: ord-9831cf0b03d44fda9b56e68fa8ae7077
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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