N-Methoxy-N-methylquinoline-6-carboxamide → 1-(Quinolin-6-yl)ethan-1-one

HRID 69152

Reaction equation

HRID 69152 reaction equation
[CH3:1][Mg]Br.CON(C)[C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2)=[O:8]>C1(C)C=CC=CC=1.C1COCC1.C1COCC1>[N:15]1[C:16]2[C:11](=[CH:10][C:9]([C:7](=[O:8])[CH3:1])=[CH:18][CH:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 55211172N-Methoxy-N-methylquinoline-6-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 2585591-(Quinolin-6-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
0 °C

Procedure

Methylmagnesium bromide (190 mL of a 1.4 M solution in toluene/THF 3:1, 270 mmol) was added over 35 min to a solution of quinoline-6-carboxylic acid methoxy-methyl-amide (Stage 1.5, 26 g, 120 mmol) in THF at 0° C. under nitrogen. The RM was stirred for 30 min at 0° C. and then allowed to warm up to rt. The RM was quenched with 1 M HCl and the THF removed under reduced pressure. The residue was taken up in EtOAc and the organic layer separated, dried and concentrated to give the title compound as a yellow solid (tR 1.0 min (conditions 1), MH+=172).

Workup

  1. temperatureto warm up to rt
  2. customThe RM was quenched with 1 M HCl
  3. customthe THF removed under reduced pressure
  4. customthe organic layer separated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b400a060e54b478684a09a7f1a29c10e
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Linked notes

Loading…