2-(2-methylphenyl)acetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared using the procedure as described in Example 80 substituting 2-chloro-3-trifluoromethylphenylhydrazine hydrochloride for phenylhydrazine hydrochloride and substituting N-formyl-2,3-dihydro-1H-indene-1-carboxamide (prepared using the procedure as described in Example 76A, substituting from indan-1-carboxamide [Seidl Tetrahedron 1964, 20, 633] for 2-o-tolylacetamide) for N-formylphenylacetamide. The residue was purified by flash chromatography (40% ethyl acetate/hexanes) to provide the title compound. MS (ESI) m/e: 364 (M+H)+; 1H NMR (DMSO-d6) δ 2.05-2.45 (m, 2H), 2.8-3.05 (m, 2H), 4.29-4.35 (t, 1H), 6.95-7.05 (bs, 1H), 7.03-7.1 (t, 1H), 7.1-7.21 (t, 1H), 7.2-7.3 (d, 1H), 7.78-7.82 (t, 2H), 8.0-8.01 (bs, 0.5H), 8.18 (s, 1H), 8.22 (bs, 0.5H); Anal. calcd. for C, 59.43; H, 3.60; N, 11.55. Found C, 59.20; H, 3.34; N, 11.48 The title compound was prepared prepared The residue was purified by flash chromatography (40% ethyl acetate/hexanes)

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-o-tolylacetamide (Lee, Dong-Ung; Mayer, Klaus K.; Wiegrebe, Wolfgang; Lauber, Rolf; Schlunegger, Urs P.; Arch. Pharm. 1988, 321; 265-272) (320 mg, 2.15 mmol) and N,N,-dimethylformamide dimethylacetal (1.1 mL, 8.59 mmol) was stirred under N2 for 55 min at 120° C. The excess of N,N,-dimethylformamide dimethylacetal was eliminated under reduced pressure. The residue was dissolved in 3 mL of 70% aqueous acetic acid and stirred at 0° C. for 30 min. The precipitate was filtered, washed with water and dried to afford the title compound as a white solid. MS (DCI/NH3) m/z 195 (M+NH4)+. stirred at 0° C. for 30 min The precipitate was filtered washed with water dried

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-o-tolylacetamide (Lee, Dong-Ung; Mayer, Klaus K.; Wiegrebe, Wolfgang; Lauber, Rolf; Schlunegger, Urs P.; Arch. Pharm. 1988, 321; 265-272) (320 mg, 2.15 mmol) and N,N,-dimethylformamide dimethylacetal (1.1 mL, 8.59 mmol) was stirred under N2 for 55 min at 120° C. The excess of N,N,-dimethylformamide dimethylacetal was eliminated under reduced pressure. The residue was dissolved in 3 mL of 70% aqueous acetic acid and stirred at 0° C. for 30 min. The precipitate was filtered, washed with water and dried to afford the title compound as a white solid. MS (DCI/NH3) m/z 195 (M+NH4)+. stirred at 0° C. for 30 min The precipitate was filtered washed with water dried