Ethanol → (8E)-3-methoxy-8-[(4-nitrophenyl)methoxyimino]-6,7-dihydro-5H-naphthalen-2-ol

HRID 41948Notes

Reaction equation

HRID 41948 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][C:3]=1[O:13][CH3:14].Cl.[N+:16]([C:19]1[CH:27]=[CH:26]C(CNO)=[CH:21][CH:20]=1)([O-:18])=[O:17].[N:28]1C=CC=CC=1.[CH2:34]([OH:36])[CH3:35]>>[N+:16]([C:19]1[CH:27]=[CH:26][C:35]([CH2:34][O:36]/[N:28]=[C:9]2\[CH2:8][CH2:7][CH2:6][C:5]3[C:10]\2=[CH:11][C:2]([OH:1])=[C:3]([O:13][CH3:14])[CH:4]=3)=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 3168407-Hydroxy-6-methoxy-1-tetraloneHCID 86662371(4-Nitrobenzyl)hydroxylamine hydrochloride

Product 1

HCID 87138499(8E)-3-methoxy-8-[(4-nitrophenyl)methoxyimino]-6,7-dihydro-5H-naphthalen-2-olYield 55%

Procedure

7-Hydroxy-6-methoxy-1-tetralone (105 mg, 0.55 mmol) was subjected to reaction with (4-nitrobenzyl)hydroxylamine hydrochloride (122 mg, 0.60 mmol) in ethanol (5 mL) and pyridine (0.5 mL, 6.45 mmol) under the same conditions as described for (E)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2R)-one O-4-nitrobenzyl oxime. The solid obtained on work up was recrystallised (isopropanol) to yield the title compound (103 mg, 55%) as off-white crystals, m.p. 125-127° C.

Workup

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

Sources & evidence

ORD record
ord-972e713bd1f74c03bd12922506f473ce
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Reaction notes

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