Potassium Carbonate → HCID 178436635, compound
Reaction equation
[CH2:1]([C:3]1[C:4]([O:12][CH3:13])=[N:5][C:6]([CH3:11])=[C:7]([CH:10]=1)[C:8]#[N:9])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:21][OH:22]>C(O)C>[CH2:1]([C:3]1[C:4]([O:12][CH3:13])=[N:5][C:6]([CH3:11])=[C:7]([CH:10]=1)[C:8]([NH:21][OH:22])=[NH:9])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a mixture of 5-ethyl-6-methoxy-2-methylnicotinonitrile (300 mg, 1.705 mmol), potassium carbonate (1.174 g, 8.51 mmol) and hydroxylamine hydrochloride (591 mg, 8.50 mmol) is added absolute ethanol (15 mL). The reaction mixture is heated at 90° C. under a reflux condenser for 22 hr. LC/MS shows the reaction is incomplete, and 2 products are observed, one consistent with the desired compound and the other consistent with the corresponding primary nicotinamide. More potassium carbonate (1.174 g, 8.51 mmol) and hydroxylamine hydrochloride (591 mg, 8.50 mmol) are added and the reaction is heated at 90° C. for a further 15 hr. The mixture is allowed to cool, filtered and the filtrate is evaporated to give a sticky, cream colored residue that is used in the next step without purification.
Sources & evidence
- ORD record
- ord-20ca0148e1924acb8e2b4d5731f58a40
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173682B2
Reaction notes
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