3-Methoxymethyl-5-nitroisoquinoline → 5-Amino-3-methoxymethylisoquinoline

HRID 1577085Notes

Reaction equation

HRID 1577085 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([N+:14]([O-])=O)[CH:10]=[CH:9][CH:8]=2>C(O)C.[Pd]>[NH2:14][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]=[C:4]([CH2:3][O:2][CH3:1])[N:5]=[CH:6]2

Participants

4

Reactant 1

HCID 128748473-Methoxymethyl-5-nitroisoquinoline

Product 1

HCID 128748525-Amino-3-methoxymethylisoquinolineYield 69.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A catalyst (3% palladium-on-charcoal; 8 g) is added to a solution of 3-methoxymethyl-5-nitroisoquinoline (78 g) in ethanol (2 liters). The resulting suspension is stirred and hydrogen is bubbled through for 6 hours, whilst keeping the temperature between 20° and 25° C. with the aid of a bath of cold water. The mixture is then filtered and the filtrate is evaporated to dryness at 60° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is recrystallised from diisopropyl ether (500 cc). 5-Amino-3-methoxymethylisoquinoline (47 g), m.p. 105° C., is obtained.

Workup

  1. customhydrogen is bubbled through for 6 hours
  2. customthe temperature between 20° and 25° C.
  3. filtrationThe mixture is then filtered
  4. customthe filtrate is evaporated to dryness at 60° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  5. customThe residue is recrystallised from diisopropyl ether (500 cc)

Sources & evidence

ORD record
ord-166d5cc6c94c44faae641d4021919f57
Source dataset
uspto-grants-1981_09
Patent number
US04287197

Reaction notes

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