Sodium sulfate decahydrate → 4-Amino-3,5-dichlorobenzylamine

HRID 917545

Reaction equation

HRID 917545 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([Cl:17])[C:15]=1[NH2:16])[C:11]#[N:12].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([Cl:17])[C:15]=1[NH2:16])[CH2:11][NH2:12]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 5227064-Amino-3,5-dichlorobenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 189757634-Amino-3,5-dichlorobenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To lithium aluminum hydride (0.57 g, 15 mmol) in dry THF (20 mL) was added dropwise 3,5-dichloro-4-aminobenzonitrile (1.87 g, 10 mmol) in THF (30 mL). The mixture was stirred at RT for 2 hours. Then, sodium sulfate decahydrate (4.83 g, 15 mmol) was added and stirred for 30 min. The solid was filtered off and washed with THF for three times. The solvent was removed by rotovap and residue was purified by column with Methanol/DCM (3:7) as the eluant. 3,5-Dichloro-4-aminobenzylamine was obtained as an off-white solid (1.5 g, 80%).

Workup

  1. stirringstirred for 30 min
  2. filtrationThe solid was filtered off
  3. washwashed with THF for three times
  4. customThe solvent was removed by rotovap and residue
  5. customwas purified by column with Methanol/DCM (3:7) as the eluant

Sources & evidence

ORD record
ord-b41ab9d80e0f4621b3ce22741867f2e3
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Linked notes

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