Benzenepropanoyl chloride → 1-Acetyl-4-phenyl-6-(3-phenylpropionyl)amino-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

HRID 557561Notes

Reaction equation

HRID 557561 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2].[C:24]1([CH2:30][CH2:31][C:32](Cl)=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)C(C)C)(C)C>O1CCCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:32](=[O:33])[CH2:31][CH2:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 64801Benzenepropanoyl chlorideHCID 81531DiisopropylethylamineHCID 28370841-(6-amino-2,2,4-trimethyl-4-phenyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

Product 1

HCID 179628861-Acetyl-4-phenyl-6-(3-phenylpropionyl)amino-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acylation of 1-acetyl-6-amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (10 mg) with 3-phenylpropionyl chloride (11 mg) and N,N-diisopropylethylamine (22 μl) in tetrahydrofuran (1 ml) was performed according to the method described in example 6.

Sources & evidence

ORD record
ord-d2b45c293d1b47649af9b6189f5ae341
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

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