Triethylamine → 6-bromo-N-methoxy-N-methylquinoline-2-carboxamide

HRID 2425561Notes

Reaction equation

HRID 2425561 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.C(N(CC)CC)C.Cl.[CH3:23][NH:24][O:25][CH3:26].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([N:24]([O:25][CH3:26])[CH3:23])=[O:14])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 123862086-Bromoquinoline-2-carboxylic acid

Product 1

HCID 574581646-bromo-N-methoxy-N-methylquinoline-2-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (1 ml) solution of 6-bromoquinoline-2-carboxylic acid (4000 mg, 15.9 mmol, US2005165049A1), triethylamine (6.64 ml, 47.6 mmol), N,O-dimethylhydroxyamine hydrochloride (1860 mg, 19.0 mmol) and HBTU (6620 mg, 17.5 mmol) were added and the mixture was stirred for 24 hours at room temperature. The reaction was quenched with saturated NaHCO3 aqueous solution and water, and the product was extracted with EtOAc 3 times. The combined organic extracts were dried over Na2SO4, and concentrated in vacuo. The crude residue was applied to a silica gel column chromatography and eluted with hexane/ethyl acetate (4:1) to furnish the title compound (4.29 g, 92% yield) as an orange solid. 1H NMR (300 MHz, CDCl3) δ 3.47 (3H, s), 3.80 (3H, s), 7.68-7.80 (1H, brs), 7.81-7.85 (1H, m), 8.00-8.06 (2H, m), 8.17 (1H, d, J=8.1 Hz). MS (ESI): m/z 295, 297 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 aqueous solution and water
  2. extractionthe product was extracted with EtOAc 3 times
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. washeluted with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-5fe7406016ff43f6a1f46caff8a198aa
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

Loading…