Water → 3-Chloro-2-methylbenzylamine

HRID 2390034Notes

Reaction equation

HRID 2390034 reaction equation
[Cl:1][C:2]1[C:3]([CH3:20])=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][N:6]1C(=O)C2=CC=CC=C2C1=O.O.NN.O>CO>[Cl:1][C:2]1[C:3]([CH3:20])=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH2:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 59323393N-(3-chloro-2-methylbenzyl)phthalimide

Product 1

HCID 27576713-Chloro-2-methylbenzylamineYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

1.15 g of N-(3-chloro-2-methylbenzyl)phthalimide was dissolved in 20 mL of methanol, and 5 mL of hydrazine monohydrate was added thereto at room temperature. Thereafter, it was warmed to 80° C., followed by continuously reacting overnight. After completion of the reaction, the reaction liquid was left to be cooled, and water was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 628 mg (yield 100%) of a title compound as a colorless clear oily substance.

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. waitwas left
  5. temperatureto be cooled
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cba0ac32b7984915918b29b89474e363
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

Loading…