Hydrazine hydrate (1:1) → 3-Phenylprop-2-en-1-amine

HRID 1774266Notes

Reaction equation

HRID 1774266 reaction equation
[CH2:1]([N:10]1C(=O)C2=CC=CC=C2C1=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.NN>CO>[CH2:1]([NH2:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 318571N-cinnamyl phthalimide

Product 1

HCID 203693-Phenylprop-2-en-1-amineYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

N-cinnamyl phthalimide (3 mmol) was mixed with 65% hydrazine hydrate (6 mmol, 2 equiv) and MeOH (10 mL), and the mixture was heated at 70° C. for 2 h. After the solvent was removed by a rotary evaporator, the solid residue was treated with 1 N NaOH (30 mL), and the resulting mixture was extracted with EtOAc (4×50 mL) and dried. Evaporation of the solvent under reduced pressure afforded the crude product, which was purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM) to give cinnamyl amine. Compound 117 (white solid) was obtained at 30% yield, and compound 119 (off-white solid) was obtained at 80% yield. Identity was confirmed by 1H NMR (400 MHz, CD3OD).

Workup

  1. customAfter the solvent was removed by a rotary evaporator
  2. additionthe solid residue was treated with 1 N NaOH (30 mL)
  3. extractionthe resulting mixture was extracted with EtOAc (4×50 mL)
  4. customdried
  5. customEvaporation of the solvent under reduced pressure
  6. customafforded the crude product, which
  7. customwas purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM)

Sources & evidence

ORD record
ord-5e6b1c4c48ea419d978617ff5620a469
Source dataset
uspto-grants-2016_02
Patent number
US09260382B2

Reaction notes

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