تفاعل #2313117

معادلة التفاعل

3-methoxy-2-methylbenzoyl chloride

sodium hydroxide

sodium hydroxide

tert-butylhydrazine hydrochloride

→

N-(3-methoxy-2-methylbenzoyl)-N'-tert-butylhydrazine

المردود 96.0%

المذيبات

water

methylene chloride

water

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added concurrently at -20° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   غسيلthe organic layer was washed with water (4×500 mL)
4. 4
   تجفيفdried over magnesium sulfate

الإجراء التجريبي

To a stirred suspension of tert-butylhydrazine hydrochloride (397 g, 3.27 mol) in methylene chloride (2 L) at 0° C., was added sodium hydroxide (50% aqueous, 260 g) diluted with water (400 mL). Following this, 3-methoxy-2-methylbenzoyl chloride (140 g, 0.78 mol) in methylene chloride (1 L) and sodium hydroxide (50% aqueous, 80 g) diluted with water (400 mL) were added concurrently at -20° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and after additional 30 minutes, the organic layer was washed with water (4×500 mL), dried over magnesium sulfate and stripped to yield N-(3-methoxy-2-methylbenzoyl)-N'-tert-butylhydrazine (177 g, 96% yield). 1H-NMR (CDCl3)δppm 1.19 (s, 9H, t-Bu), 2.29 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 6.90 (d, 1H, C-4 or 6), 6.95 (d, 1H, C-4 or C6) 7.19 (dd, 1H, C-5).

المصدر