Nitromethane → HCID 70622813, compound

HRID 1834851Notes

Reaction equation

HRID 1834851 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([CH:14]=O)=[C:8]2[C:4]=1[CH2:5][CH2:6][CH2:7]2.C([O-])(=O)C.[NH4+].[CH3:21][N+:22]([O-:24])=[O:23]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([CH:14]=[CH:21][N+:22]([O-:24])=[O:23])=[C:8]2[C:4]=1[CH2:5][CH2:6][CH2:7]2

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 12617462HCID 12617462, compound

Product 1

HCID 70622813HCID 70622813, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
112 °C

Procedure

To a 100 ml 3-necked round bottom flask fitted with a condenser and thermometer and magnetically stirred, was added 12.97 g (0.063 mole) of 4,5-dimethoxy-7-indanaldehyde, 3.00 g (0.039 mole) of ammonium acetate, 13.0 ml (0.292 mole) of CH3NO2 and 40 ml of glacial acetic acid. This mixture was heated for 1 to 2 hours at 112° C. As the reaction solution began to cool the entire solution solidified. After cooling in an ice bath and removing the solvent by filtration, the solid 4,5-dimethoxy-7-nitrovinylindane was washed with a small volume of acetic acid giving fine yellow needles (9.55 g) after thorough drying. The filtrate was poured into 300 ml of ice and water from which precipitated a slightly gummy, yellow-brown solid. This gave an additional 1.43 g of crystalline solid after drying and crystallizing from methanol giving a total yeild of 10.98 g (70%). An analytical sample melted at 128°-130° C. Anal. Calcd. for C13H15NO4 : C, 62.64; H, 6.06; N, 5.62. Found: C, 62.79; H, 6.12; N, 5.53

Workup

  1. customTo a 100 ml 3-necked round bottom flask fitted with a condenser
  2. temperatureto cool the entire solution
  3. temperatureAfter cooling in an ice bath
  4. customremoving the solvent
  5. filtrationby filtration
  6. washthe solid 4,5-dimethoxy-7-nitrovinylindane was washed with a small volume of acetic acid giving fine yellow needles (9.55 g) after thorough drying
  7. additionThe filtrate was poured into 300 ml of ice and water from which
  8. customprecipitated a slightly gummy, yellow-brown solid

Sources & evidence

ORD record
ord-f9e42165d3254122abb5eb4d010ff2a8
Source dataset
uspto-grants-1978_01
Patent number
US04071562

Reaction notes

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