Nitric Acid → HCID 13321942, compound

HRID 1284890Notes

Reaction equation

HRID 1284890 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2].[N+:19]([O-:22])([OH:21])=[O:20]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:12]([N+:19]([O-:21])=[O:20])=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([N+:19]([O-:22])=[O:20])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 13321936HCID 13321936, compound

Product 2

HCID 13321942HCID 13321942, compoundHCID 13321943HCID 13321943, compound

Procedure

0.325 g of 5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester (Example 3) is stirred in 6 ml of 65% strength nitric acid for 15 minutes at room temperature, then for one hour at 70° C. Thereafter the reaction mixture is poured into ice water and extracted with ethyl acetate. The combined ethyl acetate extracts are evaporated; the evaporation residue is chromatographed on silica gel with a mixture of equal parts of methylene chloride and acetone, thus obtaining 0.012 g of 6-nitro-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester (mp 318°-325° C.) and 0.023 g of 8-nitro-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester, mp 304°-306° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe combined ethyl acetate extracts are evaporated
  3. customthe evaporation residue is chromatographed on silica gel with a mixture of equal parts of methylene chloride and acetone

Sources & evidence

ORD record
ord-14583276b30948d6a84f057eebd5b390
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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