Nitric Acid → HCID 59168383, compound

HRID 1443933Notes

Reaction equation

HRID 1443933 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]1[C:14]2[C:15]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[N:12]3[C:13]=2[C:8]([CH2:9][CH2:10][CH2:11]3)=[CH:7][CH:6]=1.S(=O)(=O)(O)[OH:23]>O>[N+:1]([C:6]1[CH:7]=[C:8]2[C:13]3=[C:14]([C:15]4[CH2:21][CH2:20][CH2:19][CH2:18][C:17](=[O:23])[C:16]=4[N:12]3[CH2:11][CH2:10][CH2:9]2)[CH:5]=1)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 12368969HCID 12368969, compound

Product 1

HCID 59168383HCID 59168383, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Nitric acid (1.2 mL, 22 mmol) was added dropwise to a mixture of 5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinoline (2.0 g, 8.9 mmol) and concentrated sulfuric acid (43 mL). The reaction mixture was stirred for 1 hour and then poured into water and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated. The crude material was purified by flash column chromatography (elution with 12% ethyl acetate-hexanes) to provide 2-nitro-8-oxo-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinoline.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude material was purified by flash column chromatography (elution with 12% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-622ca6d4c97540cf8da704e945da5522
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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