Aniline → HCID 10457089, compound

HRID 1785897Notes

Reaction equation

HRID 1785897 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH3:22])[N:15]([C:23](=[O:32])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C@@H:14]([CH3:33])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.NC1C=CC=CC=1.COC1C=CC(C(Cl)=O)=CC=1.CN(C)C1C=CC(C(Cl)=O)=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][C:18]([CH3:19])=[CH:22][CH:20]=3)[N:15]([C:23](=[O:32])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C@@H:14]([CH3:33])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6115AnilineHCID 7477p-Anisoyl chlorideHCID 44007824-(Dimethylamino)benzoyl chlorideHCID 86592032HCID 86592032, compound

Product 1

HCID 10457089HCID 10457089, compound

Procedure

(±)-Cis-N-(4-chloro-phenyl)-N-[1-(4-methoxy-benzoyl)-2,5-dimethyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was made following general procedure B, substituting 3-toluidine for aniline and 4-methoxybenzoyl chloride for 4-dimethylaminobenzoyl chloride. The reaction was non-selective and also (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-methoxy-benzoyl)-2,7-dimethyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was obtained in a 1:1 mixture with the product.

Sources & evidence

ORD record
ord-38ef0511f95740f39c826894bf1ee9e4
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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