Ethyl Acetate → 3-Amino-5-morpholinopicolinamide

HRID 1431254Notes

Reaction equation

HRID 1431254 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([N+:15]([O-])=O)[C:10]([C:13]#[N:14])=[N:11][CH:12]=2)[CH2:3][CH2:2]1.CC[O:20]C(C)=O>>[NH2:15][C:9]1[C:10]([C:13]([NH2:14])=[O:20])=[N:11][CH:12]=[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:8]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 596311815-Morpholino-3-nitropicolinonitrile

Product 1

HCID 596313413-Amino-5-morpholinopicolinamide

Procedure

To a stirred solution of 5-morpholino-3-nitropicolinonitrile (100 mg, 0.43 mmol) in EtOAc (5 mL) was added stannous chloride, dihydrate (0.41 g, 2.13 mmol). The reaction was heated at reflux for 15 min. After this time a white solid precipitates. The suspension was filtered and the resulting solid was washed with 1.0M NaOH (10 mL) and brine (10 mL) and dried under vacuum to give 3-amino-5-morpholinopicolinamide. Mass Spectrum (ESI) m/e=223.2 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 15 min
  3. customAfter this time a white solid precipitates
  4. filtrationThe suspension was filtered
  5. washthe resulting solid was washed with 1.0M NaOH (10 mL) and brine (10 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-1e74cf66aafc42b897cf284d1f0e1372
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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