8-(Benzyloxy)-4-[(2-chloro-4-fluoro-5-methoxyphenyl)amino]-7-methoxybenzo[g]quinoline-3-carbonitrile → HCID 178486404, compound

HRID 989398Notes

Reaction equation

HRID 989398 reaction equation
C([O:8][C:9]1[C:35]([O:36][CH3:37])=[CH:34][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[CH:10]=1)[N:18]=[CH:17][C:16]([C:21]#[N:22])=[C:15]3[NH:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([F:32])=[CH:26][C:25]=1[Cl:33])C1C=CC=CC=1>C(Cl)Cl.CN(C)C=O.[Pd]>[Cl:33][C:25]1[CH:26]=[C:27]([F:32])[C:28]([O:30][CH3:31])=[CH:29][C:24]=1[NH:23][C:15]1[C:14]2[C:19](=[CH:20][C:11]3[CH:10]=[C:9]([OH:8])[C:35]([O:36][CH3:37])=[CH:34][C:12]=3[CH:13]=2)[N:18]=[CH:17][C:16]=1[C:21]#[N:22]

Participants

5

Reactant 1

HCID 101646618-(Benzyloxy)-4-[(2-chloro-4-fluoro-5-methoxyphenyl)amino]-7-methoxybenzo[g]quinoline-3-carbonitrile

Product 1

HCID 178486404HCID 178486404, compoundYield 95.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-(benzyloxy)-4-[(2-chloro-4-fluoro-5-methoxyphenyl)amino]-7-methoxybenzo[g]quinoline-3-carbonitrile (1.88 g, 3.70 mmol) and 280 mg of 15% Pd on carbon in a mixture of 50 mL of methylene chloride and 70 mL of N,N-dimethylformamide is hydrogenated at 50-40 psi for 15 hours. The mixture is filtered through Celite and concentrated in vacuo to a small volume. The yellow solid is collected by filtration to provide 1.50 g (95%) of 4-[(2-chloro-4-fluoro-5-methoxyphenyl)amino]-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile, mp 239-242° C. dec.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationconcentrated in vacuo to a small volume
  3. filtrationThe yellow solid is collected by filtration

Sources & evidence

ORD record
ord-a8995595d4d549ef871417c2180b6df8
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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