Ethanol → HCID 178455207, compound
Reaction equation
[CH3:1][C:2]([Si:5]([CH3:23])([CH3:22])[O:6][CH2:7][CH2:8][CH2:9][C:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20]#[N:21])[C:14]=2[CH:13]=[CH:12][N:11]=1)([CH3:4])[CH3:3].C(O)C.C(=O)(O)[O-].[Na+].Cl.[NH2:33][OH:34]>C(OCC)(=O)C>[CH3:4][C:2]([Si:5]([CH3:22])([CH3:23])[O:6][CH2:7][CH2:8][CH2:9][C:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20](=[NH:21])[NH:33][OH:34])[C:14]=2[CH:13]=[CH:12][N:11]=1)([CH3:1])[CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A round bottomed flask was charged with 1-(3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-5-isoquinolinecarbonitrile (D12; 417 mg, 1.28 mmol), ethanol (10 ml), sodium bicarbonate (107 mg, 12.8 mmol) and hydroxylamine hydrochloride (710 mg, 10.2 mmol). The vessel was fitted with a reflux condenser and warmed to 65° C. overnight. The resulting slurry was diluted with ethyl acetate and filtered through celite. The filtrate was concentrated in vacuo to give a yellow oil that was purified by flash column chromatography on silica using 0% to 100% ethyl acetate in cyclohexane as eluent. The relevant fractions were pooled and concentrated in vacuo to give the title compound as a yellow solid (280 mg).
Workup
- customThe vessel was fitted with a reflux condenser
- filtrationfiltered through celite
- concentrationThe filtrate was concentrated in vacuo
- customto give a yellow oil that
- customwas purified by flash column chromatography on silica using 0% to 100% ethyl acetate in cyclohexane as eluent
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b6c62ab634a145ea97f9fbbc316bf646
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329730B2
Reaction notes
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