4-Aminophenol → 6-Methoxy-1-[(4-hydroxy)phenyl]imino-1,2,3,4-tetrahydronaphthalene

HRID 1710

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.[OH:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[N:19][C:18]1[CH:20]=[CH:21][C:15]([OH:14])=[CH:16][CH:17]=1)[CH2:8][CH2:7][CH2:6]2

Participants

Reactant 2

HCID 4034-Aminophenol

HCID 141126-Methoxy-alpha-tetralone

Product 1

HCID 110109726-Methoxy-1-[(4-hydroxy)phenyl]imino-1,2,3,4-tetrahydronaphthalene

Conditions

Temperature: 180 °C

Procedure

A mixture of 6-methoxytetralone (25 g, 142 mmol) and 4-hydroxyaniline (16.3 g, 149 mmol) was heated to 180° C. under a nitrogen stream for 2 h. After cooling to ambient temperature, the solid mass was recrystallized from toluene/methanol: 1H NMR (300 MHz) d 8.15 (d, J=9.7 Hz, 1H), 6.5-7.9 (m, 6H), 3.80 (s, 3H), 2.84 (t, J=7.3 Hz, 2H), 2.51 (t, J=6.8 Hz, 2H), 1.85 (m, 2H).

Workup

temperatureAfter cooling to ambient temperature
customthe solid mass was recrystallized from toluene/methanol

Sources & evidence

ORD record: ord-9257a86a9c6c4200ba96f6bf32445239
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726186

Linked notes

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