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

HRID 280026Notes

Reaction equation

HRID 280026 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 reation 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 reation 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-8273d94d34ac4bc29cd2117b753ceb6f
Source dataset
uspto-grants-1986_05
Patent number
US04587342

Reaction notes

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