Sodium Hydroxide → HCID 20392976, compound

HRID 1863137Notes

Reaction equation

HRID 1863137 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][CH2:20][CH3:21])=[C:6]([C:8]2[N:16]=[C:15]3[C:11](=[N:12][N:13]=[N:14]3)[C:10](=[O:17])[N:9]=2)[CH:7]=1.[OH-:22].[Na+].[Mn]([O-])(=O)(=O)=[O:25].[K+]>O>[C:1]([C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][CH2:20][CH3:21])=[C:6]([C:8]2[N:16]=[C:15]3[C:11](=[N:12][N:13]=[N:14]3)[C:10](=[O:17])[N:9]=2)[CH:7]=1)([OH:25])=[O:22]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 20392966HCID 20392966, compound

Product 1

HCID 20392976HCID 20392976, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 2-(5-methyl-2-propoxyphenyl)-8-azapurin-6-one (2.85 g; prepared as described in the specifications of British Pat. No. 1338235 and U.S. Pat. No. 3,819,631) in water (80 ml) was treated with sodium hydroxide (1.0 g). Potassium permanganate (6.3 g) was then added to the resulting solution, and the mixture was stirred and heated at reflux for 150 minutes. The hot mixture was filtered through diatomaceous earth to remove manganese dioxide and the filtrate was acidified with concentrated hydrochloric acid. The solid precipitate was then dissolved in hot aqueous ammonia solution (2 N) and then acidified again with concentrated hydrochloric acid. The resulting hot suspension was then filtered and the white solid formed was washed with water. The solid was treated with ethanol (50 ml) and the resulting suspension was brought to reflux and the 2-(5-carboxy-2-propoxyphenyl)-8-azapurin-6-one (1.8 g), m.p. 271°-272° C. (with decomposition), was filtered off from the hot mixture.

Workup

  1. customprepared
  2. temperatureheated
  3. temperatureat reflux for 150 minutes
  4. filtrationThe hot mixture was filtered through diatomaceous earth
  5. customto remove manganese dioxide
  6. dissolutionThe solid precipitate was then dissolved in hot aqueous ammonia solution (2 N)
  7. filtrationThe resulting hot suspension was then filtered
  8. customthe white solid formed
  9. washwas washed with water
  10. additionThe solid was treated with ethanol (50 ml)
  11. temperatureto reflux
  12. filtrationthe 2-(5-carboxy-2-propoxyphenyl)-8-azapurin-6-one (1.8 g), m.p. 271°-272° C. (with decomposition), was filtered off from the hot mixture

Sources & evidence

ORD record
ord-82436b3ada8745bea55f7b1a3cfdb75a
Source dataset
uspto-grants-1979_09
Patent number
US04167568

Reaction notes

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