Pyridine → (3E)-6-methoxy-3-[(4-nitrophenyl)methoxyimino]-1,2-dihydroinden-5-ol

HRID 41949Notes

Reaction equation

HRID 41949 reaction equation
OC1C=C2C(CCC2=O)=CC=1OC.Cl.[N+](C1C=CC(CNO)=CC=1)([O-])=O.N1C=CC=CC=1.[N+:33]([C:36]1[CH:58]=[CH:57][C:39]([CH2:40][O:41]/[N:42]=[C:43]2\[CH2:44]C[CH2:46][C:47]3[C:52]\2=[CH:51][C:50]([O:53]C)=[C:49]([O:55][CH3:56])[CH:48]=3)=[CH:38][CH:37]=1)([O-:35])=[O:34]>C(O)C>[N+:33]([C:36]1[CH:58]=[CH:57][C:39]([CH2:40][O:41]/[N:42]=[C:43]2\[CH2:44][CH2:46][C:47]3[C:52]\2=[CH:51][C:50]([OH:53])=[C:49]([O:55][CH3:56])[CH:48]=3)=[CH:38][CH:37]=1)([O-:35])=[O:34]

Participants

6

Reactant 4

HCID 1049PyridineHCID 2331486-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-oneHCID 86662371(4-Nitrobenzyl)hydroxylamine hydrochlorideHCID 87138450(E)-6,7-dimethoxy-N-[(4-nitrophenyl)methoxy]-3,4-dihydro-2H-naphthalen-1-imine

Product 1

HCID 87138616(3E)-6-methoxy-3-[(4-nitrophenyl)methoxyimino]-1,2-dihydroinden-5-olYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Hydroxy-5-methoxy-1-indanone (114 mg, 0.64 mmol) was subjected to reaction with (4-nitrobenzyl)hydroxylamine hydrochloride (149 mg, 0.73 mmol) in ethanol (5 mL) and pyridine (0.6 mL, 7.74 mmol) under the same conditions as described for (E)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one O-4-nitrobenzyl oxime. The solid obtained on work up was recrystallized (isopropanol) to yield the title compound (101 mg, 48%) as off-white crystals, m.p. 146-149° C.

Workup

  1. customThe solid obtained on work
  2. customup was recrystallized (isopropanol)

Sources & evidence

ORD record
ord-07df91bd6c934ce29726f4ddea1a72e3
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Reaction notes

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