Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 57975900, compound
Reaction equation
O[C:2]1([C:8]([OH:10])=O)[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1.C(N(C(C)C)CC)(C)C.Cl.[CH3:21][NH:22][O:23][CH3:24].F[P-](F)(F)(F)(F)F.N1([O:41][P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C)C=O>[CH3:24][O:23][N:22]([CH3:21])[C:8]([C:2]1[C:7]([OH:41])=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:10]Participants
Procedure
2-Hydroxypicolinic acid (9.80 g, 70.45 mmol), N,N-dimethylformamide (150 ml), di-iso-propylethylamine (31 ml, 181.58 mmol), and N,O-dimethylhydroxylamine hydrochloride (7.21 g, 73.92 mmol), were stirred at 0 C. (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (38.44 g, 73.87 mmol) was added and the reaction mixture was slow warmed to room temperature. The reaction was stirred 18 hours. The mixture was concentrated and 20% 2-propanol in dichloromethane added. The mixture was washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, and concentrated. The crude material was purified by flash chromatography (0 to 50% ethyl acetate in hexanes) to give 5.21 g (41%) of 3-hydroxy-pyridine-2-carboxylic acid methoxy-methyl-amide. 1H NMR (250 MHz, CDCl3) δ 11.73 (s, 1H), 8.11 (t, J=2.9 Hz, 1H), 7.32-7.28 (m, 2H), 3.87 (s, 3H), 3.77 (s, 3H).
Workup
- concentrationThe mixture was concentrated
- addition20% 2-propanol in dichloromethane added
- washThe mixture was washed with saturated aqueous sodium bicarbonate solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe crude material was purified by flash chromatography (0 to 50% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-f78bcb73a2fd4b7fb2055f6914e307bc
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07626021B2
Reaction notes
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