Phosphorus oxychloride → HCID 9965241, compound

HRID 2213788Notes

Reaction equation

HRID 2213788 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][C:5]=2[CH:4]=1)[NH:12][CH:11]=[C:10]([C:15]#[N:16])[C:9]3=O.P(Cl)(Cl)([Cl:22])=O>CN(C)C=O>[Cl:22][C:9]1[C:8]2[C:13](=[CH:14][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:19]=[CH:18][C:6]=3[CH:7]=2)[N:12]=[CH:11][C:10]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 9942957HCID 9942957, compound

Product 1

HCID 9965241HCID 9965241, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

According to the procedure of example 101, 446.7 mg (1.8 mmol) of 8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile is refluxed in 102 mL of phosphorus oxychloride and 4 drops of N,N-dimethylformamide (DMF) for 1.5 hours to give 389.0 mg (81.6%) of 4-chloro-8-methoxy-benzo[g]quinoline-3-carbonitrile as a bright yellow solid, mp 258–260° C.

Sources & evidence

ORD record
ord-7a09dea71cb94e7a8122fea38dd0977b
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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