Tributyl(4-methoxy-2-nitrophenyl)tin → 6-(2-Amino-4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol

HRID 2423652Notes

Reaction equation

HRID 2423652 reaction equation
C([Sn](CCCC)(CCCC)C1C=CC(OC)=CC=1[N+]([O-])=O)CCC.C([O:32][C:33]1[CH:54]=[CH:53][C:36]2[CH:37]=[C:38]([C:42]3[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:43]=3[N+:50]([O-])=O)[CH2:39][CH2:40][CH2:41][C:35]=2[CH:34]=1)C1C=CC=CC=1>>[NH2:50][C:43]1[CH:44]=[C:45]([O:48][CH3:49])[CH:46]=[CH:47][C:42]=1[CH:38]1[CH2:39][CH2:40][CH2:41][C:35]2[CH:34]=[C:33]([OH:32])[CH:54]=[CH:53][C:36]=2[CH2:37]1

Participants

3

Reactant 2

HCID 23087474Tributyl(4-methoxy-2-nitrophenyl)tinHCID 697748623-benzyloxy-8-(4-methoxy-2-nitrophenyl)-6,7-dihydro-5H-benzocycloheptene

Product 1

HCID 579345186-(2-Amino-4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-olYield 72.3%

Procedure

Synthesized from 6-benzyloxy-3,4-dihydro-2H-naphthalen-1-one according to an analogous synthetic method to Preparation Example 91, 2-benzyloxy-5,7,8,9-tetrahydrobenzocyclohepten-6-one (7.2 g) was used according to an analogous synthetic method to Preparation Example 82 to provide 2-benzyloxy-8,9-dihydro-7H-benzocyclohepten-6-yl trifluoromethanesulfonate (6.7 g). Synthesized from this compound and tributyl(4-methoxy-2-nitrophenyl)tin according to an analogous synthetic method to Preparation Example 77, 3-benzyloxy-8-(4-methoxy-2-nitrophenyl)-6,7-dihydro-5H-benzocycloheptene (4.7 g) was used according to an analogous synthetic method to Example 30 to provide the title compound (2.4 g).

Sources & evidence

ORD record
ord-f67d7b4734ce464a8a616839d0baee6e
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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