Ammonia → 3-Ethoxymethyl-5-nitroisoquinoline

HRID 1577081Notes

Reaction equation

HRID 1577081 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:2].[N+:15]([O-])([OH:17])=[O:16].O.N>S(=O)(=O)(O)O>[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-:17])=[O:16])[CH:11]=[CH:10][CH:9]=2)[CH3:2]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 944Nitric AcidHCID 962WaterHCID 128748433-Ethoxymethylisoquinoline

Product 1

HCID 128748483-Ethoxymethyl-5-nitroisoquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Ethoxymethylisoquinoline (31 g) is dissolved in 95% sulphuric acid (density 1.83; 100 cc). The solution is cooled to 0° C. and a mixture of 95% sulphuric acid (density 1.83; 35 cc) and 70% nitric acid (density 1.42; 10.2 cc) is added dropwise in the course of 30 minutes so as not to exceed 10° C. Stirring is continued for 16 hours, whilst allowing the temperature to return to about 20° C. The mixture is then poured into a mixture of ice and water (1 liter), and an ammonia solution containing 20% of NH3 (density 0.9) is added, without exceeding 30° C., until a pH of about 10 is obtained. The yellow suspension is extracted with methylene chloride (4×200 cc). The organic extracts are combined, washed with water (2×50 cc), dried over magnesium sulphate and filtered and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). 3-Ethoxymethyl-5-nitroisoquinoline (24 g), melting at 54° C., is obtained.

Workup

  1. additionis added dropwise in the course of 30 minutes so as not
  2. customto exceed 10° C
  3. customto return to about 20° C
  4. additionis added
  5. customwithout exceeding 30° C., until a pH of about 10
  6. customis obtained
  7. extractionThe yellow suspension is extracted with methylene chloride (4×200 cc)
  8. washwashed with water (2×50 cc)
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)

Sources & evidence

ORD record
ord-d579ec8839b5474fb6c8a5dcfb59dc9a
Source dataset
uspto-grants-1981_09
Patent number
US04287197

Reaction notes

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