تفاعل #1269147

معادلة التفاعل

HCl

6-methoxy-8-(4-methyl-[1,4]diazepan-1-yl)-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid methyl ester

tetrahydrofuran

lithium hydroxide monohydrate

→

6-Methoxy-8-(4-methyl-[1,4]diazepan-1-yl)-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid

المذيبات

water

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred an additional 20 minutes
2. 2
   تركيزThe reaction mixture was concentrated
3. 3
   أخرىdried under high vacuum
4. 4
   أخرىto afford an orange foam

الإجراء التجريبي

To a light brown solution of 6-methoxy-8-(4-methyl-[1,4]diazepan-1-yl)-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid methyl ester (1.00 g, 2.10 mmol) in 18 mL 3:1:1 tetrahydrofuran:methanol:water was added lithium hydroxide monohydrate (0.267 g, 6.35 mmol). The reaction mixture was stirred at room temperature for 5 hours, acidified to pH 4 with 1 N HCl, and stirred an additional 20 minutes. The reaction mixture was concentrated and dried under high vacuum to afford an orange foam. 1H NMR (300 MHz, DMSO, d6) δ 11.06 (s, 1 H, NH), 7.53 (s, 1 H, C═CH), 7.00 (d, 1 H, Jm=2.4 Hz, ArH5), 6.70 (d, 1 H, Jm=2.4 Hz, ArH7), 4.05-3.99 (m, 2 H, ArNCH2CH2CH2NCH3), 3.87 (s, 3 H, OCH3), 3.68-3.60 (m, 2 H, ArNCH2CH2NCH3), 3.54-3.47 (m, 2 H, ArNCH2CH2NCH3), 3.41-3.26 (m, 2 H, ArNCH2CH2CH2NCH3), 2.82 (d, 3 H, J=4.8 Hz, NCH3), 2.46-2.41 (m, 1 H ArNCH2CH2CH2NCH3), 2.30-2.25 (m, 1H ArNCH2CH2CH2NCH3); Mass Spec.: calc. for [C17H21N3O4+H]+ Theor. m/z=332; Obs. 332.

المصدر