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

HRID 133783

Reaction equation

HRID 133783 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): δ3.65 (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-23b29a36e2744324a60f1f48f7bb42a5
Source dataset
uspto-grants-2008_06
Patent number
US07390925B2

Linked notes

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