Trifluoroacetic acid → 1,3-Dichloro-5,6,6a,7,8,12b-hexahydrobenzo[k]phenanthridine-6-carboxylic acid ethyl ester

HRID 47368

Reaction equation

HRID 47368 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[CH2:10]([C:12](=O)[C:13]([O-:15])=[O:14])[CH3:11].[CH2:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=CC1.F[C:28](F)(F)[C:29](O)=O>C(#N)C>[CH2:28]([O:15][C:13]([CH:12]1[CH:10]2[CH:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[CH2:17][CH2:11]2)[C:3]2[C:2]([Cl:1])=[CH:8][C:7]([Cl:9])=[CH:6][C:4]=2[NH:5]1)=[O:14])[CH3:29]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 99381,2-DihydronaphthaleneHCID 122813,5-DichloroanilineHCID 35932772-Ketobutyrate

Product 1

HCID 101995161,3-Dichloro-5,6,6a,7,8,12b-hexahydrobenzo[k]phenanthridine-6-carboxylic acid ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 12 was prepared in a yield of 85% by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 1,2-Dihydronaphthalene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-3d54656f7e5948219183190a4e02e3bf
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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