Ethanol → HCID 15895367, compound

HRID 1954673Notes

Reaction equation

HRID 1954673 reaction equation
[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:23]=[C:22]2[O:24][CH2:25][O:26][C:21]2=[CH:20][C:7]=1[CH2:8][N:9]1C(=O)C2=CC=CC=C2C1=O)[CH3:2].NN.C(O)C>ClCCl>[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:23]=[C:22]2[O:24][CH2:25][O:26][C:21]2=[CH:20][C:7]=1[CH2:8][NH2:9])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 15895366HCID 15895366, compound

Product 1

HCID 15895367HCID 15895367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-Ethoxymethoxy-4,5-methylenedioxybenzyl)phthalimide (1.70 g, 4.77 mmol) was treated with 0.5 mL (16 mmol) hydrazine in 90 mL refluxing ethanol for three hr. The reaction mixture was cooled and the phthalhydrazide was removed by filtration and washed three times with ethyl ether. The organic solutions were combined and evaporated to dryness on a rotary evaporator to yield a residue, which was taken up in dichloromethane. The organic solution was washed three times with 10% sodium hydroxide and the combined aqueous solutions were back-extracted with dichloromethane two times. The combined organic solutions were washed with brine and dried over sodium sulfate/potassium carbonate. Evaporation of the solvent gave of 2-ethoxymethoxy-4,5-methylenedioxybenzylamine as a slightly yellow liquid (0.98 g, 92% yield) that solidified upon standing. IR: 3298 cm-1. 1HNMR (200 MHz): δ 6.77 (1H, s); 6.75 (1H, s); 5.91 (2H, s); 5.18 (2H, s); 3.74 (2H, q, J=7.1 Hz); 3.73 (2H, s); 1.45 (2H, br s); and 1.24 ppm 3H, t,J=7.1 Hz).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe phthalhydrazide was removed by filtration
  3. washwashed three times with ethyl ether
  4. customevaporated to dryness on a rotary evaporator
  5. customto yield a residue, which
  6. washThe organic solution was washed three times with 10% sodium hydroxide
  7. extractionthe combined aqueous solutions were back-extracted with dichloromethane two times
  8. washThe combined organic solutions were washed with brine
  9. dry with materialdried over sodium sulfate/potassium carbonate
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ffafbe5bbe5a4503a799a573ee5bc739
Source dataset
uspto-grants-2000_09
Patent number
US06124278

Reaction notes

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