2-(Chloromethyl)-1-ethyl-4-nitrobenzene → HCID 20563889, compound

HRID 894143Notes

Reaction equation

HRID 894143 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[CH2:12][CH3:13]>[Pt].C(C(CC)=O)C>[CH2:12]([C:4]1[CH:5]=[CH:6][C:7]([NH:9][CH:3]([CH2:8][CH3:7])[CH2:4][CH3:5])=[CH:8][C:3]=1[CH3:2])[CH3:13]

Participants

4

Reactant 1

HCID 123759392-(Chloromethyl)-1-ethyl-4-nitrobenzene

Product 1

HCID 20563889HCID 20563889, compoundYield 237.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 7288Ethyl ketoneSolvent

Procedure

A mixture of α-chloro-2-ethyl-5-nitrotoluene (5.0 g; 0.025 mol), diethyl ketone (30 ml) and 5% platinum on carbon catalyst (Pt/C; 0.50 g) is charged to a pressure vessel. Next, the vessel is sealed, evacuated and purged with nitrogen and is then pressurized with hydrogen gas to 40 to 60 psig. The reaction mixture is agitated until the theoretical amount of hydrogen is taken up (2.5 hours). The vessel is then vented, the reaction mixture diluted with methylene chloride and filtered. The filtrate is concentrated under vacuum to yield an off-white solid (6.1 g). This solid is dissolved in 0.5 N hydrochloric acid (200 ml) at 90° C. The aqueous solution is then cooled to room temperature, extracted with ether (3x) and made alkaline. An oil separates and is removed by extraction with ether. The ether phase is washed with water, dried and concentrated under vacuum to afford 3.82 g (74.5%) of crude product, a brown oil, found to be 73.7% pure by glc.

Workup

  1. additionis charged to a pressure vessel
  2. customNext, the vessel is sealed
  3. customevacuated
  4. custompurged with nitrogen
  5. custom(2.5 hours)
  6. additionthe reaction mixture diluted with methylene chloride
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-19bfd4cd6e27409295a975360e6a939c
Source dataset
uspto-grants-1981_08
Patent number
US04282380

Reaction notes

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