(2-methoxyethyl)hydrazine synthesis

Yield:3044-15-3 50%

Reaction Conditions:

with hydrazine in ethanol;water at 0 - 45; for 13 h;

Steps:

73.1; 74.1; 75.1

Step 1: Preparation of (2-methoxyethyl)-hydrazine To a solution of hydrazine monohydrate (22 mL, 453.5 mmol) in ethanol (7 mL) at 0° C. in an ice-water bath was added 1-bromo-2-methoxy ethane (4.0 mL, 42.44 mmol) drop-wise over 20 minutes. The reaction was then allowed to warm to room temperature and stir for 40 minutes and then heated to 45° C. in a preheated oil bath for 12 hours. The reaction was then cooled to room temperature and concentrated to remove the ethanol. The remaining aqueous layer was extracted with methylene chloride (2*100 mL) and diethyl ether (2*100 mL). The organic layers were combined and dried over anhydrous Na₂SO₄, filtered and concentrated to provide (2-methoxyethyl)-hydrazine as colorless oil (2.35 g, 61%). Step 1: (2-Methoxyethyl)-hydrazine To a solution of hydrazine monohydrate (89.4 mL, 8.00 mol) in ethanol (120 mL) at 0° C. in an ice-water bath was added 1-bromo-2-methoxy ethane (18.8 mL, 0.20 mol) drop-wise over 20 minutes. The reaction was then allowed to warm to room temperature and stir for 40 minutes and then heated to 45° C. in a preheated oil bath for 12 hours. The reaction was then cooled to room temperature and concentrated to remove the ethanol. The remaining aqueous layer was extracted with methylene chloride (2*100 mL) and diethyl ether (2*100 mL). The organic layers were combined and dried over anhydrous Na₂SO₄, filtered and concentrated to provide (2-methoxyethyl)-hydrazine as a colorless oil (8.0 g, 50%).

References:

US2007/225280,2007,A1 Location in patent:Page/Page column 54; 55; 56