Pyridine → [4-(4-Acetylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 1468459Notes

Reaction equation

HRID 1468459 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:23])[CH:11]=2)[CH:6]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].N1C=CC=CC=1>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:25](=[O:27])[CH3:26])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:23])[CH:11]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86694946[4-(4-Amino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Product 1

HCID 86695034[4-(4-Acetylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl esterYield 93.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [4-(4-Amino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (115 mg, 0.34 mmol) and acetic anhydride (68.8 mg, 67 mmol) were mixed together under nitrogen and then pyridine (3 mL) was added to afford clear solution which was stirred for 10 minutes. The mixture was diluted with ethyl acetate (20 mL) and washed with 1.0 N HCl solution (10 mL), brine solution (20 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum gave [4-(4-acetylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (120 mg, 93.1%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.13 (s, 1 H), 7.94 (d, J=8.8 Hz, 1 H), 7.86 (s, 1 H), 7.76 (d, J=8.2 Hz, 2 H), 7.46 (dd, J=8.8, 1.8 Hz, 1 H), 7.11-7.19 (m, 3 H), 3.95 (s, 2 H), 3.65 (s, 3 H), 2.10 (s, 3 H), 2.07 (s, 3 H). HRMS calcd. for C22H19ClNO3 [(M−H)−.

Workup

  1. customto afford clear solution which
  2. washwashed with 1.0 N HCl solution (10 mL), brine solution (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationFiltration of the drying agent and concentration of the solvent under vacuum

Sources & evidence

ORD record
ord-d0cce89992404785ace876aa7ad75855
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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