3-Ethoxymethyl-5-nitroisoquinoline → 5-Amino-3-ethoxymethylisoquinoline

HRID 1577080Notes

Reaction equation

HRID 1577080 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]=[CH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([N+:15]([O-])=O)[CH:11]=[CH:10][CH:9]=2)[CH3:2]>C(O)C.[Pd]>[NH2:15][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH:14]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]=[CH:7]2

Participants

4

Reactant 1

HCID 128748483-Ethoxymethyl-5-nitroisoquinoline

Product 1

HCID 128748535-Amino-3-ethoxymethylisoquinolineYield 78.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A catalyst (3% palladium-on-charcoal; 3.5 g) is added to a solution of 3-ethoxymethyl-5-nitroisoquinoline (24 g) in ethanol (350 cc). A stream of hydrogen is bubbled through for 4 hours, whilst keeping the temperature at about 25° C. with the aid of a bath of cold water. The suspension is filtered and the filtrate is evaporated to dryness at 50° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is recrystallized from diisopropyl ether (200 cc). 5-Amino-3-ethoxymethylisoquinoline (16.5 g), melting at 95° C., is obtained.

Workup

  1. customA stream of hydrogen is bubbled through for 4 hours
  2. customat about 25° C.
  3. filtrationThe suspension is filtered
  4. customthe filtrate is evaporated to dryness at 50° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  5. customThe residue is recrystallized from diisopropyl ether (200 cc)

Sources & evidence

ORD record
ord-4807b768002b40699bf7957dc819ffd2
Source dataset
uspto-grants-1981_09
Patent number
US04287197

Reaction notes

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