Hydrazine hydrate (1:1) → (4-Chloro-3-methoxyphenyl)methanamine

HRID 1934710Notes

Reaction equation

HRID 1934710 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2C(=O)C3=CC=CC=C3C2=O)=[CH:4][C:3]=1[O:20][CH3:21].O.NN>C(O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22467651HCID 22467651, compound

Product 1

HCID 15548036(4-Chloro-3-methoxyphenyl)methanamineYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(4-chloro-3-methoxybenzyl)phthalimide (3.00 g) in ethanol (60 mL) was added hydrazine hydrate (2.62 mL), and the mixture was heated for an hour under reflux. The resulting precipitates were faltered off and the filtrate was evaporated in vacuo. The residue was partitioned between chloroform and an aqueous saturated sodium bicarbonate solution. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give 4-chloro-3-methoxybenzylamine as a yellow oil (1.64 g).

Workup

  1. temperaturethe mixture was heated for an hour
  2. temperatureunder reflux
  3. customThe resulting precipitates
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was partitioned between chloroform
  6. washThe separated organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-9118fe18302f486b89b864aa13dfd805
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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