2-Bromo-4-methoxy-1-nitrobenzene → 6-(2-Amino-5-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950118ノート

反応式

HRID 1950118 の反応式
C(OC1C=C2C(C=C(Br)CC2)=CC=1)C1C=CC=CC=1.BrC1C=C(OC)C=CC=1[N+]([O-])=O.C([O:39][C:40]1[CH:49]=[C:48]2[C:43]([CH:44]=[C:45]([C:50]3[CH:55]=[C:54]([O:56][CH3:57])[CH:53]=[CH:52][C:51]=3[N+:58]([O-])=O)[CH2:46][CH2:47]2)=[CH:42][CH:41]=1)C1C=CC=CC=1>>[NH2:58][C:51]1[CH:52]=[CH:53][C:54]([O:56][CH3:57])=[CH:55][C:50]=1[CH:45]1[CH2:46][CH2:47][C:48]2[CH:49]=[C:40]([OH:39])[CH:41]=[CH:42][C:43]=2[CH2:44]1

参加物

4

反応物 3

HCID 129667452-Bromo-4-methoxy-1-nitrobenzeneHCID 230874107-Benzyloxy-3-(5-methoxy-2-nitrophenyl)-1,2-dihydronaphthaleneHCID 230874203-Bromo-1,2-dihydro-7-(phenylmethoxy)naphthalene

生成物 1

HCID 230871806-(2-Amino-5-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol収率 67.7%

実験手順

To a solution of 3-bromo-4-nitrophenol (4.1 g) in N,N-dimethylformamide (40 ml) were sequentially added cesium carbonate (9.2 g) and methyl iodide (1.5 ml), and the solution was stirred overnight at room temperature. Water was added thereto, the solution was stirred, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide 2-bromo-4-methoxy-1-nitrobenzene (4.1 g). Synthesized from 7-benzyloxy-3-bromo-1,2-dihydronaphthalene and 2-bromo-4-methoxy-1-nitrobenzene according to an analogous synthetic method to Preparation Example 107, 7-benzyloxy-3-(5-methoxy-2-nitrophenyl)-1,2-dihydronaphthalene (3.4 g) was used according to an analogous synthetic method to Example 30 to provide the title compound (1.6 g).

出典と根拠

ORDレコード
ord-573c0fb2e23c4cb8bf4e0aa4807e8036
出典データセット
uspto-grants-2013_03
特許番号
US08399520B2

反応ノート

読み込み中…