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

HRID 1787553Notes

Reaction equation

HRID 1787553 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 40 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-75c0286756144202a871cac29c39630a
Source dataset
uspto-grants-2009_03
Patent number
US07511041B2

Reaction notes

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