Acetic Acid → 2-Amino-4-(4-morpholinyl)benzonitrile

HRID 1431290Notes

Reaction equation

HRID 1431290 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([N+:15]([O-])=O)[CH:8]=2)[CH2:3][CH2:2]1.C(O)(=O)C>[Zn]>[NH2:15][C:9]1[CH:8]=[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 134992654-Morpholino-2-nitrobenzonitrile

Product 1

HCID 134992832-Amino-4-(4-morpholinyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To a mixture of 4-morpholino-2-nitrobenzonitrile (388 mg, 1664 μmol) in acetic acid (6.00 mL, 104809 μmol) at rt was added all at once zinc powder (1632 mg, 24955 μmol). An exotherm developed. The reaction was stirred at ambient temperature for 2 h then filtered, and rinsed with EtOAc. The filtrate was concd under reduced pressure to afford a slightly yellow solid. Mass Spectrum (ESI) m/e=204.1 (M+1).

Workup

  1. filtrationthen filtered
  2. washrinsed with EtOAc
  3. customto afford a slightly yellow solid

Sources & evidence

ORD record
ord-6f4a4057ac604783850ee04112a798f7
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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