Nitric Acid → 2,4-Diamino-5-(7-methoxy-8-nitro-5-quinolylmethyl)pyrimidine

HRID 34464Notes

Reaction equation

HRID 34464 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[N:15]3)=[CH:4][N:3]=1.[N+:22]([O-])([OH:24])=[O:23].[OH-].[Na+]>S(=O)(=O)(O)O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([N+:22]([O-:24])=[O:23])=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[N:15]3)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 128497902,4-Diamino-5-(7-methoxy-5-quinolylmethyl)pyrimidine

Product 1

HCID 128497932,4-Diamino-5-(7-methoxy-8-nitro-5-quinolylmethyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a cold (5°) solution of 2,4-diamino-5-(7-methoxy-5-quinolylmethyl)pyrimidine (0.28 g, 1.0 mmol) in concentrated sulfuric acid (2 mL) was added dropwise 90% nitric acid (0.10 g, 1.4 mmol). After stirring at 5° for 30 min, the reaction was poured onto ice and the resulting solution taken to pH 3 with 5N sodium hydroxide. The tan solid that separated was collected then boiled in water and filtered to remove insolubles. The filtrate was taken to pH 8 with 1M sodium carbonate to precipitate the title compound (0.14 g, 42%); mp>270° dec. Anal. Calcd for C15H14N6O3 : C, 55.21; H, 4.32; N, 25.75. Found: C, 55.02, H, 4.10; N, 25.41.

Workup

  1. additionthe reaction was poured onto ice
  2. customThe tan solid that separated was collected
  3. filtrationfiltered
  4. customto remove insolubles
  5. customto precipitate the title compound (0.14 g, 42%)

Sources & evidence

ORD record
ord-b4e72f959e3e4313b056348ad9c9138c
Source dataset
uspto-grants-1988_08
Patent number
US04761475

Reaction notes

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