Hydroxyamine hydrochloride → HCID 178463716, compound
Reaction equation
Cl.[NH2:2][OH:3].[CH2:4]([N:6]([CH3:16])[C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([CH3:15])[N:14]=1)[C:10]#[N:11])[CH3:5]>CO>[CH2:4]([N:6]([CH3:16])[C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([CH3:15])[N:14]=1)[C:10]([NH:2][OH:3])=[NH:11])[CH3:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of K tert butylate (574 mg, 5.11 mL) in methanol (10 mL), hydroxylamine hydrochloride (304 mg, 4.38 mmol) is added. To the stirred suspension, a solution of 2-(ethyl-methyl-amino)-6-methyl-isonicotinonitrile (256 mg, 1.46 mmol) in methanol (10 mL) is added and the resulting mixture is stirred at 60° C. for 15 h. The mixture is filtered, and the filtrate is concentrated. The residue is treated with 1 N aq. HCl, washed with DCM and then basified by adding 1 N aq. NaOH. The mixture is extracted three times with EA. The combined EA extracts are dried over MgSO4, filtered, concentrated and dried to give the title compound as a pale yellow oil; LC-MS: tR=0.45 min, [M+1]+=209.10; 1H NMR (D6-DMSO): δ 1.06 (t, J=6.5 Hz, 3H), 2.29 (s, 3H), 2.98 (s, 3H), 3.56 (q, J=6.3 Hz, 2H), 5.82 (s, 2H), 6.64 (s, 1H), 6.69 (s, 1H), 9.74 (s, 1H).
Workup
- filtrationThe mixture is filtered
- concentrationthe filtrate is concentrated
- additionThe residue is treated with 1 N aq. HCl
- washwashed with DCM
- additionby adding 1 N aq. NaOH
- extractionThe mixture is extracted three times with EA
- dry with materialThe combined EA extracts are dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customdried
Sources & evidence
- ORD record
- ord-33da42625afd41db8470cc547a067f8e
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592460B2
Reaction notes
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