2,2-DiMethyl-2H-1,4-benzoxazin-3(4H)-one, 97%

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

Procedure: 3 g of 2-aminophenol is mixed in 23 ml of toluene with 1.8 g of sodium hydride with the addition of 50 mg of TEBA (triethylbenzylammonium chloride), and 4.4 ml of 2-bromo-2-methylpropionic acid ethyl ester is added drop by drop at ice bath temperature. After 2 hours at room temperature, it is poured onto ice water, extracted with ethyl acetate, washed with brine, the organic phase is dried with magnesium sulfate and concentrated by evaporation. After recrystallization from isopropyl ether, 278 mg of crystals results. is added drop by drop at ice bath temperature it is poured onto ice water extracted with ethyl acetate washed with brine the organic phase is dried with magnesium sulfate concentrated by evaporation After recrystallization from isopropyl ether, 278 mg of crystals results

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

Procedure: Analogously to example 6, 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one, iodomethyl pivalate and methyl 3-(4-hydroxyphenyl)hex-4-ynoate were used to obtain 3-[4-(2,2-dimethyl-3-oxo-2,3-dihydrobenzo[1,4]oxazin-4-ylmethoxy)phenyl]hex-4-ynoic acid.

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

Procedure: Analogously to example 6, 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one, iodomethyl pivalate and methyl 3-(4-hydroxyphenyl)hex-4-ynoate were used to obtain 3-[4-(2,2-dimethyl-3-oxo-2,3-dihydrobenzo[1,4]oxazin-4-ylmethoxy)phenyl]hex-4-ynoic acid.

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of LAH (3.01 g, 79.10 mmol) in THF (80 ml) at 0° C. was added 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (7.00 g, 39.5 mmol) in portions and stirred the reaction mixture at 25° C. for 1 h and then 50° C. for 3 h. Reaction mixture was quenched by the addition cold saturated sodium sulfate solution and it was filtered through celite and extracted with DCM (100 ml×2), washed with brine (50 ml), dried over sodium sulfate, concentrated to give 2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine (6.09 g), which was used as such for the next reaction without purification 50° C. for 3 h Reaction mixture was quenched by the addition cold saturated sodium sulfate solution and it was filtered through celite extracted with DCM (100 ml×2) washed with brine (50 ml) dried over sodium sulfate concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-Bromo-N-(2-hydroxy-phenyl)-2-methyl-propionamide (21.8 g, 84.4 mmol) in DMF (85 ml) at 25° C. was added potassium carbonate (23.32 g, 168.99 mmol) and stirred the reaction mixture at 80° C. for 4 h. After TLC reaction mixture was filtered through celite and diluted with ethyl acetate 500 ml and then washed with water (100 ml×3), brine (100 ml), dried over anhydrous sodium sulfate, concentrated to give 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (12.64 g) as brown solid which was purified by column chromatography to furnish 8.5 g pure compound. After TLC reaction mixture was filtered through celite diluted with ethyl acetate 500 ml washed with water (100 ml×3), brine (100 ml) dried over anhydrous sodium sulfate concentrated

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of LAH (3.01 g, 79.10 mmol) in THF (80 mL) at 0° C. was added 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (7.00 g, 39.5 mmol) in portions and stirred the reaction mixture at 25° C. for 1 h and then 50° C. for 3 h. Reaction mixture was quenched by the addition cold saturated sodium sulfate solution and it was filtered through celite and extracted with DCM (100 mL×2), washed with brine (50 mL), dried over sodium sulfate, concentrated to give 2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine (6.09 g), which was used as such for the next reaction without purification 50° C. for 3 h Reaction mixture was quenched by the addition cold saturated sodium sulfate solution and it was filtered through celite extracted with DCM (100 mL×2) washed with brine (50 mL) dried over sodium sulfate concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-Bromo-N-(2-hydroxy-phenyl)-2-methyl-propionamide (21.8 g, 84.4 mmol) in DMF (85 mL) at 25° C. was added potassium carbonate (23.32 g, 168.99 mmol) and stirred the reaction mixture at 80° C. for 4 h. After TLC reaction mixture was filtered through celite and diluted with ethyl acetate 500 mL and then washed with water (100 mL×3), brine (100 mL), dried over anhydrous sodium sulfate, concentrated to give 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (12.64 g) as brown solid which was purified by column chromatography to furnish 8.5 g pure compound. After TLC reaction mixture was filtered through celite diluted with ethyl acetate 500 mL washed with water (100 mL×3), brine (100 mL) dried over anhydrous sodium sulfate concentrated

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of LAH (3.01 g, 79.10 mmol) in THF (80 mL) at 0° C. was added 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (7.00 g, 39.5 mmol) in portions and stirred the reaction mixture at 25° C. for 1 h and then 50° C. for 3 h. Reaction mixture was quenched by the addition cold saturated sodium sulfate solution and it was filtered through celite and extracted with DCM (100 mL×2), washed with brine (50 mL), dried over sodium sulfate, concentrated to give 2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine (6.09 g), which was used as such for the next reaction without purification 50° C. for 3 h Reaction mixture was quenched by the addition cold saturated sodium sulfate solution and it was filtered through celite extracted with DCM (100 mL×2) washed with brine (50 mL) dried over sodium sulfate concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-Bromo-N-(2-hydroxy-phenyl)-2-methyl-propionamide (21.8 g, 84.4 mmol) in DMF (85 mL) at 25° C. was added potassium carbonate (23.32 g, 168.99 mmol) and stirred the reaction mixture at 80° C. for 4 h. After TLC reaction mixture was filtered through celite and diluted with ethyl acetate 500 mL and then washed with water (100 mL×3), brine (100 mL), dried over anhydrous sodium sulfate, concentrated to give 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (12.64 g) as brown solid which was purified by column chromatography to furnish 8.5 g pure compound. After TLC reaction mixture was filtered through celite diluted with ethyl acetate 500 mL washed with water (100 mL×3), brine (100 mL) dried over anhydrous sodium sulfate concentrated

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of LAH (3.01 g, 79.10 mmol) in THF (80 mL) at 0° C. was added 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (7.00 g, 39.5 mmol) in portions and stirred the reaction mixture at 25° C. for 1 h and then 50° C. for 3 h. Reaction mixture was quenched by the addition cold saturated sodium sulfate solution and it was filtered through celite and extracted with DCM (100 mL×2), washed with brine (50 mL), dried over sodium sulfate, concentrated to give 2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine (6.09 g), which was used as such for the next reaction without purification 50° C. for 3 h Reaction mixture was quenched by the addition cold saturated sodium sulfate solution and it was filtered through celite extracted with DCM (100 mL×2) washed with brine (50 mL) dried over sodium sulfate concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-Bromo-N-(2-hydroxy-phenyl)-2-methyl-propionamide (21.8 g, 84.4 mmol) in DMF (85 mL) at 25° C. was added potassium carbonate (23.32 g, 168.99 mmol) and stirred the reaction mixture at 80° C. for 4 h. After TLC reaction mixture was filtered through celite and diluted with ethyl acetate 500 mL and then washed with water (100 mL×3), brine (100 mL), dried over anhydrous sodium sulfate, concentrated to give 2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (12.64 g) as brown solid which was purified by column chromatography to furnish 8.5 g pure compound. After TLC reaction mixture was filtered through celite diluted with ethyl acetate 500 mL washed with water (100 mL×3), brine (100 mL) dried over anhydrous sodium sulfate concentrated

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

Procedure: 3 g of 2-aminophenol is mixed in 23 ml of toluene with 1.8 g of sodium hydride with the addition of 50 mg of TEBA (triethylbenzylammonium chloride), and 4.4 ml of 2-bromo-2-methylpropionic acid ethyl ester is added drop by drop at ice bath temperature. After 2 hours at room temperature, it is poured onto ice water, extracted with ethyl acetate, washed with brine, the organic phase is dried with magnesium sulfate and concentrated by evaporation. After recrystallization from isopropyl ether, 278 mg of crystals results. is added drop by drop at ice bath temperature it is poured onto ice water extracted with ethyl acetate washed with brine the organic phase is dried with magnesium sulfate concentrated by evaporation After recrystallization from isopropyl ether, 278 mg of crystals results