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

HRID 2217762Notes

Reaction equation

HRID 2217762 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 h. Then, sodium sulfate decahydrate (4.83 g, 15 mmol) was added and the mixture was stirred for 30 min. The solid was filtered off and washed with THF three times. The solvent was removed under vacuum and the residue was purified by chromatography with Methanol/DCM (3:7) as the eluant. 3,5-Dichloro-4-aminobenzylamine was obtained as an off-white solid (1.5 g, 80%). 1H NMR (300 MHz, CD3OD): δ 3.65 (s, 2H), 7.2 (s, 2H).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. filtrationThe solid was filtered off
  3. washwashed with THF three times
  4. customThe solvent was removed under vacuum
  5. customthe residue was purified by chromatography with Methanol/DCM (3:7) as the eluant

Sources & evidence

ORD record
ord-ff14a5af24b341efa3e9fe59d4850f33
Source dataset
uspto-grants-2008_08
Patent number
US07408071B2

Reaction notes

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