Hydrazine hydrate (1:1) → alpha-(5-Aminopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile

HRID 863876Notes

Reaction equation

HRID 863876 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([S:30][C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2C(=O)C3C(=CC=CC=3)C2=O)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O.NN>C(O)C>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:11]([S:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1)([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]#[N:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10673372alpha-(3,4-Dimethoxypheny)1,3-dihydro-alpha-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrile

Product 1

HCID 10572107alpha-(5-Aminopentyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrileYield 112.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.72 g of α-(3,4-dimethoxyphenyl)-1,3-dihydro-α-[(4-methylphenyl)thio]-1,3-dioxo-2H-isoindole-2-heptanenitrile, 100 mL of ethyl alcohol, and 7.0 mL of hydrazine hydrate is heated under reflux. In about a 30 minutes, a heavy precipitate forms. After 1.33 hours, the reaction is cooled to room temperature and concentrated in vacuo. The residue is warmed on a steam bath with 2N hydrochloric acid for 10 minutes. Diatomaceous silica and chloroform are added, the mixture is shaken thoroughly and then filtered through more diatoma ceous silica. The organic phase is washed first with aqueous ammonia, then brine, and, after drying (sodium sulfate), it is concentrated in vacuo to give 3.97 g of the desired product as a yellow oil. MS(CI): m/z 385(M+H). Calcd for C22H28N2O2S 5/8H2O: C=66.77, H=7.45, N=7.08, S=8.09 Found C=66.53, H=7.02, N=6.73, S=8.04

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. customIn about a 30 minutes
  4. concentrationconcentrated in vacuo
  5. temperatureThe residue is warmed on a steam bath with 2N hydrochloric acid for 10 minutes
  6. additionDiatomaceous silica and chloroform are added
  7. filtrationfiltered through more diatoma ceous silica
  8. washThe organic phase is washed first with aqueous ammonia
  9. dry with materialbrine, and, after drying (sodium sulfate), it
  10. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-6a12429f777240b3af2befb9d9dc0121
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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