Nitric Acid → 2-(2-Propoxy-5-nitrophenyl)purin-6-one

HRID 1532082Notes

Reaction equation

HRID 1532082 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:23]=[C:22]2[C:18](=[N:19][CH:20]=[N:21]2)[C:17](=[O:24])[N:16]=1)[CH2:6][CH3:7].[OH-].[NH4+]>S(=O)(=O)(O)O>[CH2:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[CH:11][C:10]=1[C:15]1[N:23]=[C:22]2[C:18](=[N:19][CH:20]=[N:21]2)[C:17](=[O:24])[N:16]=1)[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14923Ammonium HydroxideHCID 18409955HCID 18409955, compound

Product 1

HCID 212508282-(2-Propoxy-5-nitrophenyl)purin-6-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of fuming nitric acid (0.23 ml) and sulphuric acid (4 ml) was added dropwise to a stirred solution of 2-(2-propoxyphenyl)purin-6-one (1.0 g) in sulphuric acid (4 ml) at 0 to -5° C. The temperature was maintained between −5° C. and +4° C. for 20 hours and then the mixture was poured into ice-water. The filtered solution was treated with concentrated ammonium hydroxide to pH 9 to give a crude product, 0.55 g. Recrystallisation twice from aqueous ethanol then once from acetonitrile gave the title compound, 0.2 g, m.p. 254-256° C.

Workup

  1. temperatureThe temperature was maintained between −5° C. and +4° C. for 20 hours
  2. customto give a crude product, 0.55 g
  3. customRecrystallisation twice from aqueous ethanol

Sources & evidence

ORD record
ord-df8043f1e8a0452c8148afceacb91800
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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