Sodium Hydroxide → 2-Amino-4-(4-morpholinyl)benzonitrile

HRID 1091532Notes

Reaction equation

HRID 1091532 reaction equation
O.O.[Sn](Cl)Cl.[N:6]1([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([N+:20]([O-])=O)[CH:13]=2)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[OH-].[Na+]>Cl>[NH2:20][C:14]1[CH:13]=[C:12]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[CH:19]=[CH:18][C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 134992654-Morpholino-2-nitrobenzonitrile

Product 1

HCID 134992832-Amino-4-(4-morpholinyl)benzonitrileYield 95.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a cooled mixture of tin(II) chloride dihydrate 12.8 g (56.7 mmol) in conc. HCl mL with ice bath was added 4-(morpholin-4-yl)-2-nitrobenzonitrile 4.20 g (16.09 mmol) and stirred at room temperature for 2 hours. The reaction mixture was poured into diluted NaOH solution and extracted into ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4 and the solvent was evaporated. The crude product was washed with diethyl ether to give the title compound 3.13 g as off-white solid. Yield 95.0%.

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated
  5. washThe crude product was washed with diethyl ether

Sources & evidence

ORD record
ord-21ef5eb7f24949b289e1ca76d8b6b19d
Source dataset
uspto-grants-2012_03
Patent number
US08129386B2

Reaction notes

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