Morpholine → HCID 59443439, compound

HRID 1035635Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[CH:9]=2)[C:4]=1[C:21]([OH:23])=O.S(Cl)(Cl)=O.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[CH:9]=2)[C:4]=1[C:21]([N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Methoxy-6-(3-methoxyphenyl)-1-naphthoic acid (200 mg, 0.65 mmol, 1 eq) is boiled under reflux with 5 ml of thionyl chloride under a nitrogen atmosphere for 30 min according to method E. The residue is dissolved in dry THF and added to 1 ml of morpholine cooled at 0° C. The reaction mixture is boiled under reflux over night. After the solvent has been removed on a rotary evaporator, purification is effected by column chromatography with dichloromethane/methanol 95/5 as the eluent. Characterization of the compound was not effected. The raw product was directly employed for ether cleavage.

Workup

temperatureunder reflux over night
customAfter the solvent has been removed on a rotary evaporator, purification

Sources & evidence

ORD record: ord-5b5fbccba8be49ee8b4502e0177f6fb4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546392B2

Reaction notes

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