N-[(4-methoxyphenyl)methylidene]hydroxylamine

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: 4-Methoxybenzaldehyde oxime (1.63, g, 10.8 mmol) and methyl 2-(1,2,4-triazol-1-ylmethyl)acrylate. (1.50 g, 8.97 mol) were added together with 100 mL of CH2Cl2. To the above mixture was added bleach (23 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The mixture was diluted with CH2Cl2 and washed with water and brine, It was dried over MgSO4, concentrated, and chromatographed with 30-100% EtOAc in CH2Cl2 on silica gel to give 1.81 g of the desired product (66%). washed with water and brine, It was dried over MgSO4 concentrated chromatographed with 30-100% EtOAc in CH2Cl2 on silica gel

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

Procedure: 4-Methoxybenzaldehyde oxime (5.00 g, 33.1 mmol) and itaconic acid monomethyl ester (5.72 g, 39.7 mol) were added together with 200 mL of THF. To the above mixture was added bleach (84 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The THF was removed in vacuo. The aqueous mixture was acidified with aqueous HCl and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, concentrated, and chromatographed with 10-30% MeOH in CH2Cl2 on silica gel to give 5.58 g of the desired product (58%). 1H NMR (DMSO-d6): δ 3.08 (m, 2H); 3.61 (s, 3H); 3.55-3.87 (m, 2H); 3.80 (s, 3H); 7.00 (d, 2H); 7.61 (d, 2H). The THF was removed in vacuo extracted with EtOAc The EtOAc solution was washed with brine dried over MgSO4 concentrated chromatographed with 10-30% MeOH in CH2Cl2 on silica gel

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

Procedure: 4-Methoxybenzaldehyde (10.0 g, 73.4 mmol) was dissolved in 200 mL of ethanol. A solution of hydroxyamine hydrochloride (6.38 g, 91.8 mmol) in 50 mL of H2O was added followed by a solution of sodium acetate (12.1 g, 146.8 mmol) in 50 mL of H2O. The mixture was stirred at room temperature under N2 for 12 h. The ethanol was removed in vacuo and the aqueous mixture was extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, and concentrated to afford 12.8 g of light yellow oil. 1H NMR showed it was 80% pure (92% yield). This material was taken into the next step without further purification. (CDCl3): δ 2.15 (s, 1H); 3.83 (s, 3H); 6.92 (d, 2H); 7.50 (d, 2H); 8.10 (s, 1H). The ethanol was removed in vacuo the aqueous mixture was extracted with EtOAc The EtOAc solution was washed with brine dried over MgSO4 concentrated

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

Procedure: 4-Methoxybenzaldehyde oxime (1.63, g, 10.8 mmol) and methyl 2-(1,2,4-triazol-1-ylmethyl)acrylate.(1.50 g, 8.97 mol) were added together with 100 mL of CH2Cl2. To the above mixture was added bleach (23 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The mixture was diluted with CH2Cl2 and washed with water and brine, It was dried over MgSO4, concentrated, and chromatographed with 30-100% EtOAc in CH2Cl2 on silica gel to give 1.81 g of the desired product (66%). washed with water and brine, It was dried over MgSO4 concentrated chromatographed with 30-100% EtOAc in CH2Cl2 on silica gel

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

Procedure: 4-Methoxybenzaldehyde oxime (5.00 g, 33.1 mmol) and itaconic acid monomethyl ester (5.72 g, 39.7 mol) were added together with 200 mL of THF. To the above mixture was added bleach (84 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The THF was removed in vacuo. The aqueous mixture was acidified with aqueous HCl and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, concentrated, and chromatographed with 10-30% MeOH in CH2Cl2 on silica gel to give 5.58 g of the desired product (58%). 1H NMR (DMSC-d6): δ63.08 (m, 2H); 3.61 (s, 3H); 3.55-3.87 (m, 2H); 3.80 (s, 3H); 7.00 (d, 2H); 7.61 (d, 2H). The THF was removed in vacuo extracted with EtOAc The EtOAc solution was washed with brine dried over MgSO4 concentrated chromatographed with 10-30% MeOH in CH2Cl2 on silica gel

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

Procedure: 4-Methoxybenzaldehyde (10.0 g, 73.4 mmol) was dissolved in 200 mL of ethanol. A solution of hydroxyamine hydrochloride (6.38 g, 91.8 mmol) in 50 mL of H2O was added followed by a solution of sodium acetate (12.1 g, 146.8 mmol) in 50 mL of H2O. The mixture was stirred at room temperature under N2 for 12 h. The ethanol was removed in vacuo and the aqueous mixture was extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, and concentrated to afford 12.8 g of light yellow oil. 1H NMR showed it was 80% pure (92% yield). This material was taken into the next step without further purification. (CDCl3): δ2.15 (s, 1H); 3.83 (s, 3H); 6.92 (d, 2H); 7.50 (d, 2H); 8.10 (s, 1H). The ethanol was removed in vacuo the aqueous mixture was extracted with EtOAc The EtOAc solution was washed with brine dried over MgSO4 concentrated

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

Procedure: 4-Methoxybenzaldehyde oxime (1.63, g, 10.8 mmol) and methyl 2-(1,2,4-triazol-1-ylmethyl)acrylate. (1.50 g, 8.97 mol) were added together with 100 mL of CH2Cl2. To the above mixture was added bleach (23 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The mixture was diluted with CH2Cl2 and washed with water and brine, It was dried over MgSO4, concentrated, and chromatographed with 30-100% EtOAc in CH2Cl2 on silica gel to give 1.81 g of the desired product (66%). washed with water and brine, It was dried over MgSO4 concentrated chromatographed with 30-100% EtOAc in CH2Cl2 on silica gel

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

Procedure: 4-Methoxybenzaldehyde oxime (5.00 g, 33.1 mmol) and itaconic acid monomethyl ester (5.72 g, 39.7 mol) were added together with 200 mL of THF. To the above mixture was added bleach (84 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The THF was removed in vacuo. The aqueous mixture was acidified with aqueous HCl and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, concentrated, and chromatographed with 10-30% MeOH in CH2Cl2 on silica gel to give 5.58 g of the desired product (58%). 1H NMR (DMSO-d6): δ 3.08 (m, 2H); 3.61 (s, 3H); 3.55-3.87 (m, 2H); 3.80 (s, 3H); 7.00 (d, 2H); 7.61 (d, 2H). The THF was removed in vacuo extracted with EtOAc The EtOAc solution was washed with brine dried over MgSO4 concentrated chromatographed with 10-30% MeOH in CH2Cl2 on silica gel

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

Procedure: 4-Methoxybenzaldehyde oxime (5.00 g, 33.1 mmol) and itaconic acid monomethyl ester (5.72 g, 39.7 mol) were added together with 200 mL of THF. To the above mixture was added bleach (84 mL of 0.67M aqueous solution) dropwise at room temperature. The reaction mixture was then stirred at RT under N2 for 12 h. The THF was removed in vacuo. The aqueous mixture was acidified with aqueous HCl and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, concentrated, and chromatographed with 10-30% MeOH in CH2Cl2 on silica gel to give 5.58 g of the desired product (58%). 1H NMR (DMSO-d6): δ 3.08 (m, 2H); 3.61 (s, 3H); 3.55-3.87 (m, 2H); 3.80 (s, 3H); 7.00 (d, 2H); 7.61 (d, 2H). The THF was removed in vacuo extracted with EtOAc The EtOAc solution was washed with brine dried over MgSO4 concentrated chromatographed with 10-30% MeOH in CH2Cl2 on silica gel

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

Procedure: 4-Methoxybenzaldehyde (10.0 g, 73.4 mmol) was dissolved in 200 mL of ethanol. A solution of hydroxyamine hydrochloride (6.38 g, 91.8 mmol) in 50 mL of H2O was added followed by a solution of sodium acetate (12.1 g, 146.8 mmol) in 50 mL of H2O. The mixture was stirred at room temperature under N2 for 12 h. The ethanol was removed in vacuo and the aqueous mixture was extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, and concentrated to afford 12.8 g of light yellow oil. 1H NMR showed it was 80% pure (92% yield). This material was taken into the next step without further purification. (CDCl3): δ 2.15 (s, 1H); 3.83 (s, 3H); 6.92 (d, 2H); 7.50 (d, 2H); 8.10 (s, 1H). The ethanol was removed in vacuo the aqueous mixture was extracted with EtOAc The EtOAc solution was washed with brine dried over MgSO4 concentrated