Acetaminophen → HCID 57699928, compound

HRID 1686016Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=1>CN1C(=O)CCC1.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:22][C:23]3[CH:24]=[CH:25][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:27][CH:28]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Twelve carousel tubes were charged with 7-benzyloxy-4-chloro-6-methoxy-quinoline (12×2.00 g, 12×6.67 mmol) and N-(4-hydroxy-phenyl)-acetamide (12×3.03 g, 12×20.00 mmol, 3.0 eq) in NMP (12×2.00 ml) and heated under to nitrogen to 150° C. for 2.5 hours. The reaction mixtures were allowed to cool to room temperature, diluted with DCM (12×20 ml). The combined organic solutions were washed with 2N NaOH (3×200 ml), water (200 ml), brine (200 ml), dried (MgSO4), filtered and concentrated under reduced pressure to leave a brown oil. Purification by column chromatography (4% methanol in DCM) afforded the title compound as a beige solid (36.73 g).

Workup

customThe reaction mixtures
temperatureto cool to room temperature
washThe combined organic solutions were washed with 2N NaOH (3×200 ml), water (200 ml), brine (200 ml)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customto leave a brown oil
customPurification by column chromatography (4% methanol in DCM)

Sources & evidence

ORD record: ord-5afa799c34604b22821e878c82fc624e
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148531B2

Reaction notes

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