E-8-(4-Acetoxy-3-methoxybenzylidene)-5,6,7,8-tetrahydro-4-methylquinoline → E-5,6,7,8-Tetrahydro-8-[4-hydroxy-3-methoxybenzylidene]-4-methylquinoline

HRID 464323Notes

Reaction equation

C([O:4][C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[C:10]2\[CH2:11][CH2:12][CH2:13][C:14]3[C:15]([CH3:20])=[CH:16][CH:17]=[N:18][C:19]\2=3)=[CH:7][C:6]=1[O:23][CH3:24])(=O)C>Cl>[OH:4][C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[C:10]2\[CH2:11][CH2:12][CH2:13][C:14]3[C:15]([CH3:20])=[CH:16][CH:17]=[N:18][C:19]\2=3)=[CH:7][C:6]=1[O:23][CH3:24]

Participants

Conditions

Temperature: 90 °C

Procedure

E-8-(4-Acetoxy-3-methoxybenzylidene)-5,6,7,8-tetrahydro-4-methylquinoline, HCl (from Example 1) (1.3 g) was dissolved in 2N HCl (20 ml) and heated at 90° C. for 4 hours. The resulting red solid was removed by filtration, washed with a small amount of ether and finally dried to give the title compound as the hydrochloride salt (1.15 g) m.p. 285°-287° C.

Workup

customThe resulting red solid was removed by filtration
washwashed with a small amount of ether
customfinally dried

Sources & evidence

ORD record: ord-80e0c19d21314999997c43e668000b20
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04547510

Reaction notes

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