Water → HCID 54401717, compound

HRID 1834852Notes

Reaction equation

HRID 1834852 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH:20]=[CH:21][N+:22]([O-])=O)=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2.O>CCOCC>[CH3:7][O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH2:20][CH2:21][NH2:22])=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 70622813HCID 70622813, compound

Product 1

HCID 54401717HCID 54401717, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a slurry of 15.0 g (0.395 mole) of LiAlH4 and 500 ml of anhydrous ether in a 5 liter 3-necked flask fitted with a condenser, mechanical stirrer and dropping funnel was added 20.0 g (0.084 mole) of 4,5-dimethoxy-7-nitrovinylindane dissolved in 2 liters of ether. The addition was made over a period of about 4 hours while refluxing the ether slurry. When the addition was completed, refluxing was continued for an additional 1 to 2 hours. After the addition of 20 g of diatomaceous earth and then 70 ml of water slowly, dropwise, with cooling in an ice bath, the supernatant ether was decanted, the salts were washed with fresh ether several times followed by decantation and finally filtration. The solvent was removed by distillation and more thoroughly on a rotary evaporator. Cooling in an ice bath gave 15.91 g (90%) of 4,5-dimethoxy-7-aminoethylindane as a slightly yellow solid, m.p., 45°-48° C. High vacuum distillation gave an analytical sample. Anal. Calcd. for C13H19NO2 : C, 70.55; H, 8.65; N, 6.32. Found: C, 70.22; H, 8.49; N, 6.18.

Workup

  1. additionThe addition
  2. additionWhen the addition
  3. temperaturerefluxing
  4. waitwas continued for an additional 1 to 2 hours
  5. additionAfter the addition of 20 g of diatomaceous earth
  6. customthe supernatant ether was decanted
  7. washthe salts were washed with fresh ether several times
  8. filtrationfollowed by decantation and finally filtration
  9. customThe solvent was removed by distillation and more thoroughly on a rotary evaporator
  10. temperatureCooling in an ice bath

Sources & evidence

ORD record
ord-50b35440399e4f0aa993d4a350d9f8ee
Source dataset
uspto-grants-1978_01
Patent number
US04071562

Reaction notes

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