Phenol → N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

HRID 1785919Notes

Reaction equation

FC1C=CC(C([Cl:8])=O)=CC=1.C1(O)C=CC=CC=1.[OH:18][C:19]1[CH:48]=[CH:47][C:22]([C:23]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]([N:35]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:36](=[O:39])[CH2:37]C)[CH2:27][CH:26]2[CH3:46])=[O:24])=[CH:21][CH:20]=1>>[Cl:8][C:43]1[CH:44]=[CH:45][C:40]([N:35]([C@H:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:25]([C:23](=[O:24])[C:22]3[CH:47]=[CH:48][C:19]([OH:18])=[CH:20][CH:21]=3)[C@@H:26]([CH3:46])[CH2:27]2)[C:36](=[O:39])[CH3:37])=[CH:41][CH:42]=1

Participants

Reactant 3

HCID 996Phenol

HCID 678794-Fluorobenzoyl chloride

HCID 21093193(+/-)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide

Product 1

HCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Procedure

(2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was prepared was made following general procedure C, substituting 3-methoxybenzoyl chloride for 4-fluorobenzoyl chloride. Further elaboration to the phenol was done following the same procedure as described for (±)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide.

Sources & evidence

ORD record: ord-52c7f3ae7670408d9755bccd1a1bed37
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504508B2

Reaction notes

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