Ammonia → 3-Methoxymethyl-5-nitroisoquinoline

HRID 1577086Notes

Reaction equation

HRID 1577086 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.[N+:14]([O-])([OH:16])=[O:15].O.N>S(=O)(=O)(O)O>[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-:16])=[O:15])[CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 944Nitric AcidHCID 962WaterHCID 205718083-Methoxymethylisoquinoline

Product 1

HCID 128748473-Methoxymethyl-5-nitroisoquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Methoxymethylisoquinoline (68.8 g) is dissolved in 95% sulphuric acid (density 1.83; 300 cc). The solution is cooled to 0° C. and a mixture of 70% nitric acid (density 1.42; 25 cc) and 95% sulphuric acid (density 1.83; 100 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 (2 liters), 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 resulting yellow solution is extracted with methylene chloride (4×400 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-Methoxymethyl-5-nitroisoquinoline (78 g), m.p. 91° 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 resulting yellow solution is extracted with methylene chloride (4×400 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-ada006fed35c4ad882073d79299d39c3
Source dataset
uspto-grants-1981_09
Patent number
US04287197

Reaction notes

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