HCID 53889118, compound → HCID 54016375, compound

HRID 1902552Notes

Reaction equation

HRID 1902552 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:8]=[CH:9]2)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:8]=[CH:9]2

Participants

4

Reactant 1

HCID 53889118HCID 53889118, compound

Product 1

HCID 54016375HCID 54016375, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 5-nitroisoquinoline-3-acetate (20 g) is dissolved in ethyl acetate (1 liter), and a catalyst consisting of palladium-on-carbon (3/97 by weight; 21 g) is added. The mixture is hydrogenated at atmospheric pressure, at a temperature of about 50° C., for 2 hours. It is filtered through diatomaceous silica and the filtrate is then concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 50° C. to yield ethyl 5-aminoisoquinoline-3-acetate (15.8 g) in the form of beige crystals, m.p.=90° C.

Workup

  1. additionis added
  2. filtrationIt is filtered through diatomaceous silica
  3. concentrationthe filtrate is then concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 50° C.

Sources & evidence

ORD record
ord-15136facbe2d41e7973a74e745e0b6d5
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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