2-aminobenzene-1,3-diol;hydrochloride

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

Procedure: 2-Aminoresorcinol hydrochloride (2 g) and triethylchloroformate (4.5 ml) were heated to reflux under nitrogen for 3 h. After cooling to room temperature, the reaction mixture was poured into a mixture of water (70 ml) and ethanol (20 ml). The mixture was stirred vigorously for 30 minutes, then left to stand at room temperature overnight. The beige precipitate which formed was collected by filtration, and dried by azeotroping with toluene to give the title compound as a beige solid (1.2 g). to reflux under nitrogen for 3 h left to stand at room temperature overnight The beige precipitate which formed was collected by filtration dried by azeotroping with toluene

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

Procedure: 2-Aminoresorcinol hydrochloride (2 g) and triethylchloroformate (4.5 ml) were heated to reflux under nitrogen for 3 h. After cooling to room temperature, the reaction mixture was poured into a mixture of water (70 ml) and ethanol (20 ml). The mixture was stirred vigorously for 30 minutes, then left to stand at room temperature overnight. The beige precipitate which formed was collected by filtration, and dried by azeotroping with toluene to give the title compound as a beige solid (1.2 g). to reflux under nitrogen for 3 h left to stand at room temperature overnight The beige precipitate which formed was collected by filtration dried by azeotroping with toluene

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-aminoresorcinol hydrochloride (5.0 g) and triethylorthopropionate (13.7 ml) was heated to 150° C. for 2 h before being poured into a mixture of water (140 ml) and ethanol (35 ml). The mixture was stirred vigorously for 30 minutes at room temperature. The resulting precipitate was removed by filtration and dried to give the title compound as a beige solid (4.11 g). The resulting precipitate was removed by filtration dried

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-aminoresorcinol hydrochloride (5.0 g) and triethylorthopropionate (13.7 ml) was heated to 150° C. for 2 h before being poured into a mixture of water (140 ml) and ethanol (35 ml). The mixture was stirred vigorously for 30 minutes at room temperature. The resulting precipitate was removed by filtration and dried to give the title compound as a beige solid (4.11 g). The resulting precipitate was removed by filtration dried

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

Procedure: A mixture of aminoresorcinol hydrochloride (1.1 g), potassium ethyl xanthate (1.2 g) and potassium carbonate (1.0 g) was dissolved in ethanol/water (1:1, 20 ml) and (under an argon balloon) heated under reflux for 3 hours. The pale yellow solution was cooled to RT and then acetic acid (2 ml) was added to make the solution slightly acidic (gas evolution). A cream precipitate soon formed and the sealed flask was kept in the fridge overnight. The cream solid was collected by filtration and the damp product (0.9 g) was used immediately in the next step. (under an argon balloon) heated under reflux for 3 hours A cream precipitate soon formed was kept in the fridge overnight The cream solid was collected by filtration

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

Procedure: A mixture of aminoresorcinol hydrochloride (1.1 g), potassium ethyl xanthate (1.2 g) and potassium carbonate (1.0 g) was dissolved in ethanol/water (1:1, 20 ml) and (under an argon balloon) heated under reflux for 3 hours. The pale yellow solution was cooled to RT and then acetic acid (2 ml) was added to make the solution slightly acidic (gas evolution). A cream precipitate soon formed and the sealed flask was kept in the fridge overnight. The cream solid was collected by filtration and the damp product (0.9 g) was used immediately in the next step. (under an argon balloon) heated under reflux for 3 hours A cream precipitate soon formed was kept in the fridge overnight The cream solid was collected by filtration

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

Procedure: A mixture of aminoresorcinol hydrochloride (1.1 g), potassium ethyl xanthate (1.2 g) and potassium carbonate (1.0 g) was dissolved in ethanol/water (1:1, 20 ml) and (under an argon balloon) heated under reflux for 3 hours. The pale yellow solution was cooled to RT and then acetic acid (2 ml) was added to make the solution slightly acidic (gas evolution). A cream precipitate soon formed and the sealed flask was kept in the fridge overnight. The cream solid was collected by filtration and the damp product (0.9 g) was used immediately in the next step. (under an argon balloon) heated under reflux for 3 hours A cream precipitate soon formed was kept in the fridge overnight The cream solid was collected by filtration

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

Procedure: 2-Aminoresorcinol hydrochloride (2 g) and triethylchloroformate (4.5 ml) were heated to reflux under nitrogen for 3 h. After cooling to room temperature, the reaction mixture was poured into a mixture of water (70 ml) and ethanol (20 ml). The mixture was stirred vigorously for 30 minutes, then left to stand at room temperature overnight. The beige precipitate which formed was collected by filtration, and dried by azeotroping with toluene to give the title compound as a beige solid (1.2 g). to reflux under nitrogen for 3 h left to stand at room temperature overnight The beige precipitate which formed was collected by filtration dried by azeotroping with toluene

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-aminoresorcinol hydrochloride (5.0 g) and triethylorthopropionate (13.7 ml) was heated to 150° C. for 2 h before being poured into a mixture of water (140 ml) and ethanol (35 ml). The mixture was stirred vigorously for 30 minutes at room temperature. The resulting precipitate was removed by filtration and dried to give the title compound as a beige solid (4.11 g). The resulting precipitate was removed by filtration dried

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

Procedure: A mixture of 2-amino-benzene-1,3-diol hydrochloride (2.00 g, 12.4 mmol) and trimethyl orthoacetate (15 mL) was treated with concentrated sulfuric acid (5 drops) and the resulting mixture heated at reflux for 3 h, cooled and allowed to stand at room temperature overnight. The resulting mixture was concentrated in vacuo and the residue treated with ethyl acetate (200 mL), washed with water (200 mL) and brine (100 mL). The combined aqueous phases were extracted with ethyl acetate (200 mL) and the combined organic phases washed with brine and dried over sodium sulfate. The mixture was filtered and concentrated in vacuo which afforded benzooxazol-4-ol (0.94 g, 51%) as a yellow solid. the resulting mixture heated at reflux for 3 h cooled The resulting mixture was concentrated in vacuo the residue treated with ethyl acetate (200 mL) washed with water (200 mL) and brine (100 mL) The combined aqueous phases were extracted with ethyl acetate (200 mL) the combined organic phases washed with brine dried over sodium sulfate The mixture was filtered concentrated in vacuo which

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

Procedure: A mixture of 2-amino-benzene-1,3-diol hydrochloride (2.00 g, 12.4 mmol) and trimethyl orthoacetate (15 mL) was treated with concentrated sulfuric acid (5 drops) and the resulting mixture heated at reflux for 3 h, cooled and allowed to stand at room temperature overnight. The resulting mixture was concentrated in vacuo and the residue treated with ethyl acetate (200 mL), washed with water (200 mL) and brine (100 mL). The combined aqueous phases were extracted with ethyl acetate (200 mL) and the combined organic phases washed with brine and dried over sodium sulfate. The mixture was filtered and concentrated in vacuo which afforded benzooxazol-4-ol (0.94 g, 51%) as a yellow solid. the resulting mixture heated at reflux for 3 h cooled The resulting mixture was concentrated in vacuo the residue treated with ethyl acetate (200 mL) washed with water (200 mL) and brine (100 mL) The combined aqueous phases were extracted with ethyl acetate (200 mL) the combined organic phases washed with brine dried over sodium sulfate The mixture was filtered concentrated in vacuo which

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

Procedure: A mixture of aminoresorcinol hydrochloride (1.1 g), potassium ethyl xanthate (1.2 g) and potassium carbonate (1.0 g) was dissolved in ethanol/water (1:1, 20 ml) and (under an argon balloon) heated under reflux for 3 hours. The pale yellow solution was cooled to RT and then acetic acid (2 ml) was added to make the solution slightly acidic (gas evolution). A cream precipitate soon formed and the sealed flask was kept in the fridge overnight. The cream solid was collected by filtration and the damp product (0.9 g) was used immediately in the next step. (under an argon balloon) heated under reflux for 3 hours A cream precipitate soon formed was kept in the fridge overnight The cream solid was collected by filtration