Nitromethane → HCID 14969234, compound

HRID 266163Notes

Reaction equation

HRID 266163 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:17][CH2:18][CH3:19])[C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][CH2:7]2.[N+:20](C)([O-:22])=[O:21]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-:22])=[O:21])=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:17][CH2:18][CH3:19])[C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][CH2:7]2

Participants

3

Reactant 2

HCID 6375NitromethaneHCID 15647037HCID 15647037, compound

Product 1

HCID 14969234HCID 14969234, compoundYield 31%

Procedure

To an ice-cold solution of compound 6 (12.5 g, 44.5 mmol) in nitromethane (100 ml) was added (dropwise) "nitrating acid" (32.6 ml) (see synthesis of compound 3) until all starting material was consumed (monitored with gas chromatography after basification of analytical samples and extraction with Et2O). Ice-water/Et2O was added, shaken and extracted one additional time (Et2O). The combined organic extracts were dried (Na2SO4), filtered and the solvent was evaporated (12.5 g, 87%). The resulting residue was chromatographed using flash chromatography on a silica column, using petroleum ether/E2O (1:2) as eluant, yielding 4.5 g (31%) of 8-chloro-5-nitro-2-(N-n-propyl-N-propionylamino)tetralin (7a) and 3.5 g (24% of 8-chloro-7-nitro-2-(N-n-propyl-N-propionylamino)tetralin (7b). Unseparated material could be recycled in second chromatography.

Workup

  1. customwas consumed
  2. extraction(monitored with gas chromatography after basification of analytical samples and extraction with Et2O)
  3. additionIce-water/Et2O was added
  4. extractionextracted one additional time (Et2O)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated (12.5 g, 87%)
  8. customThe resulting residue was chromatographed

Sources & evidence

ORD record
ord-6798f76da3414dc09b66cbddb93ee6d0
Source dataset
uspto-grants-1997_07
Patent number
US05650427

Reaction notes

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