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

HRID 2423689Notes

Reaction equation

HRID 2423689 reaction equation
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

Participants

4

Reactant 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

Product 1

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

Procedure

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).

Sources & evidence

ORD record
ord-d58c746f0b6045929b4cd161754bfbb5
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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