N-(dimethoxymethyl)-N-ethylethanamine

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

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

Procedure: A mixture of 4-amino-3-pyridinol (3.90 g), N,N-diethylformamide dimethyl acetal (11.68 g) and toluene (20 mL) was heated under nitrogen for 2 hours. The solution was concentrated under reduced pressure. The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid. Recrystallization of the purified product from ethyl acetate/hexanes afforded 4.21 g of crystalline solid, m.p. 104°-106° C. was heated under nitrogen for 2 hours The solution was concentrated under reduced pressure The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid Recrystallization of the purified product from ethyl acetate/hexanes

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

Procedure: A mixture of 4-amino-3-pyridinol (3.90 g), N,N-diethylformamide dimethyl acetal (11.68 g) and toluene (20 mL) was heated under nitrogen for 2 hours. The solution was concentrated under reduced pressure. The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid. Recrystallization of the purified product from ethyl acetate/hexanes afforded 4.21 g of crystalline solid, m.p. 104°-106° C. was heated under nitrogen for 2 hours The solution was concentrated under reduced pressure The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid Recrystallization of the purified product from ethyl acetate/hexanes

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

Procedure: A mixture of 4-amino-3-pyridinol (3.90 g), N,N-diethylformamide dimethyl acetal (11.68 g) and toluene (20 mL) was heated under nitrogen for 2 hours. The solution was concentrated under reduced pressure. The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid. Recrystallization of the purified product from ethyl acetate/hexanes afforded 4.21 g of crystalline solid, m.p. 104°-106° C. was heated under nitrogen for 2 hours The solution was concentrated under reduced pressure The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid Recrystallization of the purified product from ethyl acetate/hexanes

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

Procedure: A mixture of 4-amino-3-pyridinol (3.90 g), N,N-diethylformamide dimethyl acetal (11.68 g) and toluene (20 mL) was heated under nitrogen for 2 hours. The solution was concentrated under reduced pressure. The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid. Recrystallization of the purified product from ethyl acetate/hexanes afforded 4.21 g of crystalline solid, m.p. 104°-106° C. was heated under nitrogen for 2 hours The solution was concentrated under reduced pressure The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid Recrystallization of the purified product from ethyl acetate/hexanes

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

Procedure: A mixture of 4-amino-3-pyridinol (3.90 g), N,N-diethylformamide dimethyl acetal (11.68 g) and toluene (20 mL) was heated under nitrogen for 2 hours. The solution was concentrated under reduced pressure. The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid. Recrystallization of the purified product from ethyl acetate/hexanes afforded 4.21 g of crystalline solid, m.p. 104°-106° C. was heated under nitrogen for 2 hours The solution was concentrated under reduced pressure The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid Recrystallization of the purified product from ethyl acetate/hexanes

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

Procedure: A mixture of 4-amino-3-pyridinol (3.90 g), N,N-diethylformamide dimethyl acetal (11.68 g) and toluene (20 mL) was heated under nitrogen for 2 hours. The solution was concentrated under reduced pressure. The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid. Recrystallization of the purified product from ethyl acetate/hexanes afforded 4.21 g of crystalline solid, m.p. 104°-106° C. was heated under nitrogen for 2 hours The solution was concentrated under reduced pressure The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid Recrystallization of the purified product from ethyl acetate/hexanes

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

Procedure: A mixture of 4-amino-3-pyridinol (3.90 g), N,N-diethylformamide dimethyl acetal (11.68 g) and toluene (20 mL) was heated under nitrogen for 2 hours. The solution was concentrated under reduced pressure. The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid. Recrystallization of the purified product from ethyl acetate/hexanes afforded 4.21 g of crystalline solid, m.p. 104°-106° C. was heated under nitrogen for 2 hours The solution was concentrated under reduced pressure The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid Recrystallization of the purified product from ethyl acetate/hexanes

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

Procedure: A mixture of 4-amino-3-pyridinol (3.90 g), N,N-diethylformamide dimethyl acetal (11.68 g) and toluene (20 mL) was heated under nitrogen for 2 hours. The solution was concentrated under reduced pressure. The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid. Recrystallization of the purified product from ethyl acetate/hexanes afforded 4.21 g of crystalline solid, m.p. 104°-106° C. was heated under nitrogen for 2 hours The solution was concentrated under reduced pressure The resulting liquid was filtered through silica gel with 10% ethanol in tetrahydrofuran to give a solid Recrystallization of the purified product from ethyl acetate/hexanes

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

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

Procedure: 42.0 g (0.16 mol) of 2-methyl-1-nitroanthraquinone (0.16 mol) and 46.2 g (0.32 mol) of diethylaminodimethoxymethane (0.32 mol) in 150 g of diethylformamide are refluxed for 7 hours. After all the volatiles have been distilled off, the residue is slurried in water and filtered with suction, and the filter residue is dried under reduced pressure. This gives 49.6 g (90.0%) of 2-(2'-diethylaminoethenyl)-1-nitroanthraquinone; melting point: 235°-241° C. (with decomposition). After all the volatiles have been distilled off filtered with suction the filter residue is dried under reduced pressure

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

Procedure: 790 G (7.8moles) of N,N-diethylformamide were treated with 985 g of dimethyl sulfate while stirring, in the course of which the temperature of the mixture rose to 40°C. After stirring overnight, the reaction mixture was allowed to run into 7.8 mols of sodium methylate in methanol (total volume approximately 2.3 liters) at 0° to 5°C, while stirring, and the batch was again stirred overnight. Thereafer the methanol was first distilled from the crystal paste, following which the desired product was distilled off at 10 mm Hg up to a bath temperature of 17°C and was fractionated through a column. 862 g (75% of theory) of N,N-diethylformamide-dimethylacetal of boiling point 70°C/50 mm Hg (with foaming) and refractive index nD24 = 1.4074 were obtained. rose to 40°C After stirring overnight while stirring Thereafer the methanol was first distilled from the crystal paste was distilled off at 10 mm Hg up to a bath temperature of 17°C