Ethanol → HCID 13321941, compound

HRID 1284889Notes

Reaction equation

HRID 1284889 reaction equation
[N+:1]([C:4]1[C:12]2[NH:11][C:10]3[CH:13]=[N:14][C:15]([C:17]([OH:19])=[O:18])=[N:16][C:9]=3[C:8]=2[CH:7]=[C:6]([N+:20]([O-:22])=[O:21])[CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[CH2:28](O)[CH3:29]>>[CH2:28]([O:18][C:17]([C:15]1[N:14]=[CH:13][C:10]2[NH:11][C:12]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]([N+:20]([O-:22])=[O:21])=[CH:7][C:8]=3[C:9]=2[N:16]=1)=[O:19])[CH3:29]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13321940HCID 13321940, compound

Product 1

HCID 13321941HCID 13321941, compound

Procedure

Under argon, 0.2 g of 6,8-dinitro-5H-pyrimido[5,4-b]indole-2-carboxylic acid (Example 8) is refluxed in 20 ml of ethanol with the addition of 1 ml of concentrated sulfuric acid for 8 hours. Subsequently the solution is concentrated to half the quantity and dissolved in methylene chloride. The solution is washed first with water, then with sodium bicarbonate solution, and finally again with water, dried, and concentrated, yielding 0.18 g of 6,8-dinitro-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester, mp 295°-299° C.

Workup

  1. concentrationSubsequently the solution is concentrated to half the quantity
  2. dissolutiondissolved in methylene chloride
  3. washThe solution is washed first with water
  4. dry with materialwith sodium bicarbonate solution, and finally again with water, dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-27209a9575964335b17577f23dcd5f0b
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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