Benzene → HCID 86592013, compound

HRID 1785878Notes

Reaction equation

[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@H:11]([N:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19](=[O:22])[CH2:20][CH3:21])[CH2:10][C@@H:9]2[CH3:29])=[O:7])=[CH:4][CH:3]=1.C(O)(=O)CC.[CH:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH3:40][C:39]1[N:1]([C:2]2[CH:3]=[CH:4][C:5]([C:6]([N:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C@H:11]([N:18]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:19](=[O:22])[CH2:20][CH3:21])[CH2:10][C@@H:9]3[CH3:29])=[O:7])=[CH:30][CH:31]=2)[C:42]([CH3:41])=[CH:37][CH:38]=1

Participants

Reactant 3

HCID 241Benzene

HCID 1032Propionic Acid

HCID 86592010HCID 86592010, compound2×

Product 1

HCID 86592013HCID 86592013, compoundYield 80%

Procedure

(±)-Cis-N-{1-[4-(2,5-dimethyl-pyrrol-1-yl)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-phenyl-propionamide was prepared from (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide. A solution of (±)-cis-N-[1-(4-amino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide (150 mg, 0.36 mmol), and propionic acid (0.5 ml) in dry benzene (20 ml) was heated at reflux under argon in a flask equipped with a Dean-Stark trap while stirring with the exclusion of light. The resulting solution was cooled to room temperature, and concentrated under vacuum. Recovered oil was purified by silica gel chromatography, eluting with hexane-ethyl acetate (3:1) to give the title compound (140 mg, 80%).

Workup

temperatureat reflux under argon in a flask
customequipped with a Dean-Stark trap
concentrationconcentrated under vacuum
customRecovered oil
customwas purified by silica gel chromatography
washeluting with hexane-ethyl acetate (3:1)

Sources & evidence

ORD record: ord-afd5bdb5e9ec4016b8f7918cf852fbd9
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

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