Acetonitrile → N-Methoxy-N-methyl-4-(2-quinolin-2-yl-ethyl)-benzamide

HRID 33866Notes

Reaction equation

HRID 33866 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1.C(#N)C.Cl.[CH3:26][O:27][NH:28][CH3:29].[OH-].[Na+]>O1CCOCC1.C(N(CC)CC)C>[CH3:26][O:27][N:28]([CH3:29])[C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 685763074-(2-Quinolin-2-yl-ethyl)-benzoic acid

Product 1

HCID 86249320N-Methoxy-N-methyl-4-(2-quinolin-2-yl-ethyl)-benzamideYield 88%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(2-Quinolin-2-yl-ethyl)-benzoic acid (530 mg) in dioxane 5 ml/acetonitrile 5 ml was added triethylamine (0.60 ml) and O,N-Dimethyl-hydroxylamine hydrogen chloride (240 mg). After 72 h, the reaction mixture was poured into 1N sodium hydroxide solution and extracted with chloroform, dried magnesium sulfate, filtered and concentrated. Biotage MPLC chromatography eluting with 20-50% ethyl acetate provided the title compound (516 mg, 88%). MS: (M+H m/z=321.1).

Workup

  1. extractionextracted with chloroform, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washBiotage MPLC chromatography eluting with 20-50% ethyl acetate

Sources & evidence

ORD record
ord-6d3e54542bd0421ba53f0b6ecb57c14b
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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