Sodium sulfate decahydrate → N-(4-(aminomethyl)-2,6-dichlorophenyl)acetamide

HRID 133785

Reaction equation

HRID 133785 reaction equation
[C:1]([NH:4][C:5]1[C:12]([Cl:13])=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[Cl:14])(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[C:1]([NH:4][C:5]1[C:6]([Cl:14])=[CH:7][C:8]([CH2:9][NH2:10])=[CH:11][C:12]=1[Cl:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 2735977N-(2,6-dichloro-4-cyanophenyl)acetamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 58962993N-(4-(aminomethyl)-2,6-dichlorophenyl)acetamideYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step B (2): To a solution of 4-acetamido-3,5-dichloro-benzonitrile (114 mg, 0.5 mmol) in 5 mL of THF was added lithium aluminum hydride (120 mg, 3.2 mmol) in one portion and the resulting mixture was stirred for 3 h. Sodium sulfate decahydrate (1 g, 3.2 mmol) was added in one portion and the mixture was stirred for 30 min. The solid was filtered off and the filtrate was concentrated. The residue was purified by HPLC to give 4-acetamido-3,5-dichloro-benzylamine (35 mg, 30%). 1H NMR (500 MHz, CD3OD): δ 7.46 (s, 2 H), 3.78 (s, 2H), 2.18 (s, 3 H).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-cc504b15272a48c7a93affceaa977dc8
Source dataset
uspto-grants-2008_06
Patent number
US07390925B2

Linked notes

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