Hydrochloric Acid → HCID 19792101, compound

HRID 1655456Notes

Reaction equation

HRID 1655456 reaction equation
Cl.[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=2[N+:34]([O-])=O)[C:18](=O)[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][CH:11]=1)#[N:3]>[Fe].CO>[CH2:19]([C:18]1[N:17]([CH2:16][C:13]2[CH:14]=[CH:15][C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:2]#[N:3])=[CH:11][CH:12]=2)[C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=2[N:34]=1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19792167HCID 19792167, compound

Product 1

HCID 19792101HCID 19792101, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a mixture of conc. HCl (4.0 ml) and methanol (10 ml) was added methyl 4-[N-(2'-cyanobiphenyl-4-yl)methyl-N-valerylamino]-3-nitrobenzoate (3.5 g). To the resultant mixture was added, with stirring, iron powder (1.3 g) in portions and the mixture was stirred for one hour at 70-80° C., followed by filtering off an insoluble material. The filtrate was concentrated, which was dissolved in ethyl acetate, washed with water, dried and concentrated to dryness. The resultant syrup was purified by column chromatography on silica gel to afford a yellow syrup (1.7 g, 53%).

Workup

  1. filtrationby filtering off an insoluble material
  2. concentrationThe filtrate was concentrated
  3. dissolutionwhich was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe resultant syrup was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5d9f2fe549ce42f39d8e853f59463777
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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