반응 #7725

반응 방정식

lithium hydroxide monohydrate

4-(3-Fluoro-benzyloxy)-2-nitro-benzoic acid

4-(3-fluorobenzyloxy)-2-nitro-benzoic acid (3-fluoro-benzyl) ester

4-(3-fluoro-benzyloxy)-2-nitro-benzoic acid methyl ester

THF

sodium hydroxide

→

title compound

수율 65.0%

2-[7-(3-Fluoro-benzyloxy)-2-methyl-4-oxo-4H-quinazolin-3-yl]-acetamide

수율 65.0%

용매

water

반응 조건

후처리

1. 1
   추출the mixture extracted with diethyl ether (3×150 mL)
2. 2
   workup.ADDITIONThen the mixture was poured into sodium hydroxide (2 N, 50 mL)
3. 3
   추출the mixture extracted with diethyl ether (3×100 mL)
4. 4
   세척The combined extracts were then washed with brine (100 mL)
5. 5
   기타dried
6. 6
   기타evaporated

실험 절차

4-(3-Fluoro-benzyloxy)-2-nitro-benzoic acid: A mixture of 4-(3-fluorobenzyloxy)-2-nitro-benzoic acid (3-fluoro-benzyl) ester and 4-(3-fluoro-benzyloxy)-2-nitro-benzoic acid methyl ester (14.0 g, 35.0 mmol) in THF (120 mL) and water (120 mL), containing lithium hydroxide monohydrate (2.94 g, 70.1 mmol) was stirred at rt for 48 h. Then the mixture was poured into sodium hydroxide (2 N, 50 mL) and then the mixture extracted with diethyl ether (3×150 mL). The aqueous phase was then adjusted to pH 2 with HCl. Then the mixture was poured into sodium hydroxide (2 N, 50 mL) and the aqueous phase was then adjusted to pH 5.2 with HCl then the mixture extracted with diethyl ether (3×100 mL). The combined extracts were then washed with brine (100 mL) dried and evaporated to afford title compound (6.6 g, 65%) as a light yellow solid. MS: m/e=290.0 (M−H).

출처