3-Nitrobenzaldehyde → 7-methoxy-2-(3-nitrobenzylidene)-3,4-dihydro-2H-napthalen-1-one

HRID 1684613Notes

Reaction equation

HRID 1684613 reaction equation
N1CCCC1.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][C:15]2=[O:18])=[CH:10][CH:9]=1.[N+:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O)([O-:21])=[O:20]>CO>[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[CH:25][C:24]3[CH:27]=[CH:28][CH:29]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=3)[C:15]2=[O:18])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 31268PyrrolidineHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 7486827-methoxy-2-(3-nitrobenzylidene)-3,4-dihydro-2H-napthalen-1-oneYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 mL (30.1 mmol) of pyrrolidine were added to a room temperature (about 25° C.) solution of 5.30 g (30.1 mmol) of 7-methoxy-1-tetraione and 4.55 g (30.1 mmol) of 3-nitrobenzaldehyde in 25 mL methanol. The reaction flask was fitted with a soxhlet extractor containing a thimble filled with 3 Å molecular sieves and a reflux condenser was placed on top of the soxhlet extractor. The reaction mixture was heated to reflux under N2 for 18 hours, cooled to room temperature and filtered. The precipitate was washed twice with CH3OH, and then dried on the funnel for 24 hours to yield 6.62 g of light tan powder. (71% yield).

Workup

  1. customThe reaction flask was fitted with a soxhlet extractor
  2. additioncontaining a thimble
  3. additionfilled with 3 Å molecular sieves and a reflux condenser
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux under N2 for 18 hours
  6. filtrationfiltered
  7. washThe precipitate was washed twice with CH3OH
  8. customdried on the funnel for 24 hours
  9. customto yield 6.62 g of light tan powder

Sources & evidence

ORD record
ord-76bce38a3e044d8ab2387173af64b6fb
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

Loading…