HCID 86732789, compound → HCID 86732790, compound

HRID 525923Notes

Reaction equation

HRID 525923 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([N+:16]([O-])=O)[C:9]3[O:15][CH2:14][O:13][C:10]=3[CH:11]=2)[C:6](=[O:19])[C:5]([C:20]([OH:22])=[O:21])=[N:4]1)[CH3:2]>C(O)(=O)C.Cl.[Pd]>[NH2:16][C:8]1[C:9]2[O:15][CH2:14][O:13][C:10]=2[CH:11]=[C:12]2[C:7]=1[C:6](=[O:19])[C:5]([C:20]([OH:22])=[O:21])=[N:4][N:3]2[CH2:1][CH3:2]

Participants

5

Reactant 1

HCID 86732789HCID 86732789, compound

Product 1

HCID 86732790HCID 86732790, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 1-ethyl-5-nitro-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid (4.25 g, 13.83 mmol) in Acetic Acid (100 mL) and hydrochloric acid (30 mL) in parr shaker bottle was added Pd/C (0.6 g, 5.64 mmol) and the mixture was hydrogenated at 50 psi on a parr shaker for 5 h. The mixture was filtered. The filtrate was allowed to drop into 500 ml of water and the precipitate was collected by filtration, dried to afford 5-amino-1-ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid (3.6 g, 12.99 mmol, 94% yield). LCMS: (M+H)+: 278.2

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-cb169c559ae3478a89bb66b9801a346c
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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