8-Benzyloxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile → HCID 178486405, compound

HRID 989374Notes

Reaction equation

HRID 989374 reaction equation
C([O:8][C:9]1[C:25]([O:26][CH3:27])=[CH:24][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[CH:10]=1)[NH:18][CH:17]=[C:16]([C:21]#[N:22])[C:15]3=[O:23])C1C=CC=CC=1>CN(C)C=O.CCOCC.[Pd]>[OH:8][C:9]1[C:25]([O:26][CH3:27])=[CH:24][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][C:11]=2[CH:10]=1)[NH:18][CH:17]=[C:16]([C:21]#[N:22])[C:15]3=[O:23]

Participants

5

Reactant 1

HCID 117726788-Benzyloxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Product 1

HCID 178486405HCID 178486405, compoundYield 154.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3.6 g (7.3 mmol) of 8-benzyloxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile and 0.7 g of 10% Pd/C in 240 mL of dimethyl formamide is hydrogenated in a Parr shaker at 40 psi for 24 hours. The catalyst is filtered through a pad of Celite, washed with dimethyl formamide and the solvent is reduced in vacuo to yield a solid. The crude product is suspended in ether, collected by filtration, further washed with ether and dried to yield 3.0 g of 8-hydroxy-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile as a yellow solid, mp>300° C.

Workup

  1. filtrationThe catalyst is filtered through a pad of Celite
  2. washwashed with dimethyl formamide
  3. customto yield a solid
  4. filtrationcollected by filtration
  5. washfurther washed with ether
  6. customdried

Sources & evidence

ORD record
ord-efb7028b0b6149ab8cbe8e1ea3b5fa5e
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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