Potassium Nitrate → HCID 44248848, compound

HRID 1443896Notes

Reaction equation

HRID 1443896 reaction equation
[CH:1]1[C:10]2[C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1.[N+:18]([O-])([O-:20])=[O:19].[K+]>S(=O)(=O)(O)O>[N+:18]([C:2]1[CH:3]=[C:4]2[C:9]3=[C:10]([C:11]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=4[N:8]3[CH2:7][CH2:6][CH2:5]2)[CH:1]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 12368969HCID 12368969, compound

Product 1

HCID 44248848HCID 44248848, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Following the procedure of Block et al. (J. Med. Chem. 2002, 45, 3509), 5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinoline (1 g, 4.4 mmol) was stirred in concentrated sulfuric acid (12 mL) at 0° C. for 30 min and then KNO3 (0.45 g, 4.4 mmol) was introduced in portions. The reaction mixture was stirred for 2 hours at 0° C. and was then poured into ice water and extracted with ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated to give 0.95 g of 2-nitro-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinoline as a brown solid. MS (ESI) m/z 271

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2f4a66522a434d2d8f64d8ec57188905
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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