Potassium Nitrate → HCID 12764429, compound

HRID 1155096Notes

Reaction equation

HRID 1155096 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[C:6]([N:9]1[CH:16]2[CH2:17][N:12]([C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[CH2:15]2)[CH2:11][CH2:10]1)(=[O:8])[CH3:7]>S(=O)(=O)(O)O>[C:6]([N:9]1[CH:16]2[CH2:17][N:12]([C:13]3[CH:21]=[C:20]([N+:1]([O-:4])=[O:2])[CH:19]=[CH:18][C:14]=3[CH2:15]2)[CH2:11][CH2:10]1)(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 12764428HCID 12764428, compound

Product 1

HCID 12764429HCID 12764429, compoundYield 6.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Potassium nitrate (13.14 g.) was added in portions to a solution of 4-acetyl-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (26.43 g.) in concentrated sulfuric acid (100 ml.). The mixture was stirred for about three days at room temperature, then quenched in ice (1500 ml.). The resulting mixture was basified with aqueous sodium hydroxide (35%) and extracted with chloroform. The chloroform extract was dried over potassium carbonate, treated with charcoal, filtered and stripped of solvent. Recrystallization of the residue from isopropyl alcohol afforded 4-acetyl-9-nitro-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (2.2 g., m.r. 142°-144° C. with resolidification and remelting, m.r. 162°-164° C.), the compound of Formula III wherein Q* is acetyl.

Workup

  1. customquenched in ice (1500 ml.)
  2. extractionextracted with chloroform
  3. extractionThe chloroform extract
  4. dry with materialwas dried over potassium carbonate
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. customRecrystallization of the residue from isopropyl alcohol

Sources & evidence

ORD record
ord-ea3ef225af1a4328a673c7dac966bd87
Source dataset
uspto-grants-1981_11
Patent number
US04299830

Reaction notes

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