Triethylamine → N-methoxy-N-methylquinoline-3-carboxamide
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=O)[CH:2]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>ClCCl>[CH3:18][O:17][N:16]([CH3:15])[C:11]([C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:13]Participants
Procedure
To a suspension of the quinoline-3-carboxylic acid (480 mg, 2.77 mmol) and N,O-dimethyhydroxylamine hydrochloride (405 mg, 4.15 mmol), in dichloromethane (10 mL) was added triethyl amine (1.93 mL, 13.8 mmol) followed by bromo(trispyrrolidin-1yl)phosphonium hexafluorophosphate (1.55 g, 3.32 mmol). After stirring the reaction mixture at room temperature for 1 hour, it was quenched by the addition of water (10 mL). The resulting mixture was extracted with DCM. The organic layer dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 75% ethyl acetate-hexanes. 1H NMR (500 MHz, CDCl3): 8.25 (d, J=1.8 Hz, 1H), 8.67 (d, J=1.3 Hz, 1H), 8.18 (d, J=8.5 Hz, 1H), 7.96 (d, J=8.2 Hz, 1H), 7.84 (t, J=8.0 Hz, 1H), 7.65 (t, J=8.5 Hz, 1H), 3.61 (s, 3H), 3.48 (s, 3H). LC-MS: 1.24 min; (M+H)=217.1.
Workup
- customit was quenched by the addition of water (10 mL)
- extractionThe resulting mixture was extracted with DCM
- dry with materialThe organic layer dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
- custom1.24 min
Sources & evidence
- ORD record
- ord-018bd5d5693e48ac9449993e11ac29ed
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625938B2
Reaction notes
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