ethyl 2-amino-4-bromobenzoate

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

Procedure: At room temperature, a solution of 3.09 g (0.0127 mol) of ethyl 2-amino-4-bromobenzoate and 30 ml absolute ethanol was saturated with dry hydrogen chloride gas. A colorless precipitate formed in the warm solution. When it was again at room temperature, the solution was diluted with 30 ml of diethyl ether; the resulting crystalline product was filtered and washed with diethyl ether. Thus there was obtained 2.72 g (77%) of the title compound: m.p. 147°-150° C. Analysis calculated for C9H11BrClNO2 : C, 38.53; H, 3.95; N, 4.99%. Found: C, 38.48; H; 4.02; N, 4.99%. At room temperature A colorless precipitate formed in the warm solution was again at room temperature the resulting crystalline product was filtered washed with diethyl ether

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

Procedure: A solution of 119 g (0.461 mol) of 2-acetylamino-4-bromobenzoic acid and 3 liters of absolute ethanol was cooled to 0° C. and was then saturated with a stream of dry hydrogen chloride gas. The solution was then heated under reflux for 24 hours. Upon cooling to room temperature, the solution was evaporated to about 750 ml and then poured into 2 liters of aqueous saturated sodium bicarbonate. The aqueous phase was extracted three times with 300 ml portions of chloroform. The combined extracts were dried over anhydrous sodium sulfate, filtered, and evaporated to afford 23.8 g (21%) of ethyl 2-amino-4-bromobenzoate as an oil: ir(CHCl3) 3504 cm, 3390, 1685, 1610, 1580 among others; 1H-NMR(CDCl3) 1.3 ppm (triplet, 3H, CH2CH3), 4.3 (quartet, 2H, CH2CH3), 5.8 (broad singlet, 2H, NH2), 6.6 [doublet of AB pattern), 1H, aromatic H.], 6.8 (singlet, 1H, aromatic H), 7.7 [doublet (part of AB pattern), 1H, aromatic H]. The solution was then heated under reflux for 24 hours the solution was evaporated to about 750 ml poured into 2 liters of aqueous saturated sodium bicarbonate The aqueous phase was extracted three times with 300 ml portions of chloroform The combined extracts were dried over anhydrous sodium sulfate filtered evaporated

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

Procedure: At room temperature, a solution of 3.09 g (0.0127 mol) of ethyl 2-amino-4-bromobenzoate and 30 ml absolute ethanol was saturated with dry hydrogen chloride gas. A colorless precipitate formed in the warm solution. When it was again at room temperature, the solution was diluted with 30 ml of diethyl ether; the resulting crystalline product was filtered and washed with diethyl ether. Thus there was obtained 2.72 g (77%) of the title compound: m.p. 147°-150° C. Analysis calculated for C9H11BrClNO2 : C, 38.53; H, 3.95; N, 4.99%. Found: C, 38.48; H; 4.02; N, 4.99%. At room temperature A colorless precipitate formed in the warm solution was again at room temperature the resulting crystalline product was filtered washed with diethyl ether

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

Procedure: A solution of 119 g (0.461 mol) of 2-acetylamino-4-bromobenzoic acid and 3 liters of absolute ethanol was cooled to 0° C. and was then saturated with a stream of dry hydrogen chloride gas. The solution was then heated under reflux for 24 hours. Upon cooling to room temperature, the solution was evaporated to about 750 ml and then poured into 2 liters of aqueous saturated sodium bicarbonate. The aqueous phase was extracted three times with 300 ml portions of chloroform. The combined extracts were dried over anhydrous sodium sulfate, filtered, and evaporated to afford 23.8 g (21%) of ethyl 2-amino-4-bromobenzoate as an oil: ir(CHCl3) 3504 cm, 3390, 1685, 1610, 1580 among others; 1H-NMR(CDCl3) 1.3 ppm (triplet, 3H, CH2CH3), 4.3 (quartet, 2H, CH2CH3), 5.8 (broad singlet, 2H, NH2), 6.6 [doublet of AB pattern), 1H, aromatic H.], 6.8 (singlet, 1H, aromatic H), 7.7 [doublet (part of AB pattern), 1H, aromatic H]. The solution was then heated under reflux for 24 hours the solution was evaporated to about 750 ml poured into 2 liters of aqueous saturated sodium bicarbonate The aqueous phase was extracted three times with 300 ml portions of chloroform The combined extracts were dried over anhydrous sodium sulfate filtered evaporated

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

Procedure: At room temperature, a solution of 3.09 g (0.0127 mol) of ethyl 2-amino-4-bromobenzoate and 30 ml absolute ethanol was saturated with dry hydrogen chloride gas. A colorless precipitate formed in the warm solution. When it was again at room temperature, the solution was diluted with 30 ml of diethyl ether; the resulting crystalline product was filtered and washed with diethyl ether. Thus there was obtained 2.72 g (77%) of the title compound: m.p. 147°-150° C. Analysis calculated for C9H11BrClNO2 : C, 38.53; H, 3.95; N, 4.99%. Found: C, 38.48; H; 4.02; N, 4.99%. At room temperature A colorless precipitate formed in the warm solution was again at room temperature the resulting crystalline product was filtered washed with diethyl ether

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

Procedure: A solution of 119 g (0.461 mol) of 2-acetylamino-4-bromobenzoic acid and 3 liters of absolute ethanol was cooled to 0° C. and was then saturated with a stream of dry hydrogen chloride gas. The solution was then heated under reflux for 24 hours. Upon cooling to room temperature, the solution was evaporated to about 750 ml and then poured into 2 liters of aqueous saturated sodium bicarbonate. The aqueous phase was extracted three times with 300 ml portions of chloroform. The combined extracts were dried over anhydrous sodium sulfate, filtered, and evaporated to afford 23.8 g (21%) of ethyl 2-amino-4-bromobenzoate as an oil: ir(CHCl3) 3504 cm, 3390, 1685, 1610, 1580 among others; 1H-NMR(CDCl3) 1.3 ppm (triplet, 3H, CH2CH3), 4.3 (quartet, 2H, CH2CH3), 5.8 (broad singlet, 2H, NH2), 6.6 [doublet (part of AB pattern), 1 H, aromatic H], 6.8 (singlet, 1H, aromatic H), 7.7 [doublet (part of AB pattern), 1H, aromatic H]. The solution was then heated under reflux for 24 hours the solution was evaporated to about 750 ml poured into 2 liters of aqueous saturated sodium bicarbonate The aqueous phase was extracted three times with 300 ml portions of chloroform The combined extracts were dried over anhydrous sodium sulfate filtered evaporated

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

Procedure: At room temperature, a solution of 3.09 g (0.0127 mol) of ethyl 2-amino-4-bromobenzoate and 30 ml absolute ethanol was saturated with dry hydrogen chloride gas. A colorless precipitate formed in the warm solution. When it was again at room temperature, the solution was diluted with 30 ml of diethyl ether; the resulting crystalline product was filtered and washed with diethyl ether. Thus there was obtained 2.72 g (77%) of the title compound: m.p. 147°-150° C. Analysis calculated for C9H11BrClNO2 : C, 38.53; H, 3.95; N, 4.99%. Found: C, 38.48; H; 4.02; N, 4.99%. At room temperature A colorless precipitate formed in the warm solution was again at room temperature the resulting crystalline product was filtered washed with diethyl ether

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

Procedure: A solution of 119 g (0.461 mol) of 2-acetylamino-4-bromobenzoic acid and 3 liters of absolute ethanol was cooled to 0° C. and was then saturated with a stream of dry hydrogen chloride gas. The solution was then heated under reflux for 24 hours. Upon cooling to room temperature, the solution was evaporated to about 750 ml and then poured into 2 liters of aqueous saturated sodium bicarbonate. The aqueous phase was extracted three times with 300 ml portions of chloroform. The combined extracts were dried over anhydrous sodium sulfate, filtered, and evaporated to afford 23.8 g (21%) of ethyl 2-amino-4-bromobenzoate as an oil: ir(CHCl3) 3504 cm, 3390, 1685, 1610, 1580 among others; 1H-NMR(CDCl3) 1.3 ppm (triplet, 3H, CH2CH3), 4.3 (quartet, 2H, CH2CH3), 5.8 (broad singlet, 2H, NH2), 6.6 [doublet (part of AB pattern), 1 H, aromatic H], 6.8 (singlet, 1H, aromatic H), 7.7 [doublet (part of AB pattern), 1H, aromatic H]. The solution was then heated under reflux for 24 hours the solution was evaporated to about 750 ml poured into 2 liters of aqueous saturated sodium bicarbonate The aqueous phase was extracted three times with 300 ml portions of chloroform The combined extracts were dried over anhydrous sodium sulfate filtered evaporated

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

Procedure: At room temperature, a solution of 3.09 g (0.0127 mol) of ethyl 2-amino-4-bromobenzoate and 30 ml absolute ethanol was saturated with dry hydrogen chloride gas. A colorless precipitate formed in the warm solution. When it was again at room temperature, the solution was diluted with 30 ml of diethyl ether; the resulting crystalline product was filtered and washed with diethyl ether. Thus there was obtained 2.72 g (77%) of the title compound: m.p. 147°-150° C. At room temperature A colorless precipitate formed in the warm solution was again at room temperature the resulting crystalline product was filtered washed with diethyl ether

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

Procedure: A solution of 119 g (0.461 mol) of 2-acetylamino-4-bromobenzoic acid and 3 liters of absolute ethanol was cooled to 0° C. and was then saturated with a stream of dry hydrogen chloride gas. The solution was then heated under reflux for 24 hours. Upon cooling to room temperature, the solution was evaporated to about 750 ml and then poured into 2 liters of aqueous saturated sodium bicarbonate. The aqueous phase was extracted three times with 300 ml portions of chloroform. The combined extracts were dried over anhydrous sodium sulfate, filtered, and evaporated to afford 23.8 g (21%) of ethyl 2-amino-4-bromobenzoate as an oil: ir(CHCl3) 3504 cm, 3390, 1685, 1610, 1580 among others; 1H--NMR(CDCl3) 1.3 ppm triplet, 3H, CH2CH3), 4.3 (quartet, 2H, CH2CH3), 5.8 (broad singlet, 2H, NH2), 6.6 [doublet (part of AB pattern), 1H, aromatic H], 6.8 (singlet, 1H, aromatic H), 7.7 [doublet (part of AB pattern), 1H, aromatic H]. The solution was then heated under reflux for 24 hours the solution was evaporated to about 750 ml poured into 2 liters of aqueous saturated sodium bicarbonate The aqueous phase was extracted three times with 300 ml portions of chloroform The combined extracts were dried over anhydrous sodium sulfate filtered evaporated

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

Procedure: At room temperature, a solution of 3.09 g (0.0127 mol) of ethyl 2-amino-4-bromobenzoate and 30 ml absolute ethanol was saturated with dry hydrogen chloride gas. A colorless precipitate formed in the warm solution. When it was again at room temperature, the solution was diluted with 30 ml of diethyl ether; the resulting crystalline product was filtered and washed with diethyl ether. Thus there was obtained 2.72 g (77%) of the title compound: m.p. 147°-150° C. Analysis calculated for C9H11BrClNO2 : C, 38.53; H, 3.95; N, 4.99%. Found: C, 38.48; H; 4.02; N, 4.99%. At room temperature A colorless precipitate formed in the warm solution was again at room temperature the resulting crystalline product was filtered washed with diethyl ether

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

Procedure: A solution of 119 g (0.461 mol) of 2-acetylamino-4-bromobenzoic acid and 3 liters of absolute ethanol was cooled to 0° C. and was then saturated with a stream of dry hydrogen chloride gas. The solution was then heated under reflux for 24 hours. Upon cooling to room temperature, the solution was evaporated to about 750 ml and then poured into 2 liters of aqueous saturated sodium bicarbonate. The aqueous phase was extracted three times with 300 ml portions of chloroform. The combined extracts were dried over anhydrous sodium sulfate, filtered, and evaporated to afford 23.8 g (21%) of ethyl 2-amino-4-bromobenzoate as an oil: ir(CHCl3) 3504 cm, 3390, 1685, 1610, 1580 among others; 1H-NMR(CDCl3) 1.3 ppm (triplet, 3H, CH2CH3), 4.3 (quartet, 2H, CH2CH3), 5.8 (broad singlet, 2H, NH2), 6.6 [doublet of AB pattern), 1H, aromatic H.], 6.8 (singlet, 1H, aromatic H), 7.7 [doublet (part of AB pattern), 1H, aromatic H]. The solution was then heated under reflux for 24 hours the solution was evaporated to about 750 ml poured into 2 liters of aqueous saturated sodium bicarbonate The aqueous phase was extracted three times with 300 ml portions of chloroform The combined extracts were dried over anhydrous sodium sulfate filtered evaporated