Water → 3-Morpholino-5-nitropyridin-4-amine

HRID 1397093Notes

Reaction equation

HRID 1397093 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[NH2:8].CCOC(C)=O.O.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>>[O:22]1[CH2:23][CH2:24][N:19]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=2[NH2:8])[CH2:20][CH2:21]1

Participants

5

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8857Ethyl AcetateHCID 49975884-Amino-3-bromo-5-nitropyridine

Product 1

HCID 583779133-Morpholino-5-nitropyridin-4-amine

Procedure

A solution of 3-bromo-5-nitropyridin-4-amine (XLVI) (1 eq.), in neat morpholine in a sealed tube was heated at 120-140° C. overnight. The solution was poured into a mixture of EtOAc and water. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic layers was washed with brine, dried over MgSO4 and concentrated to get a residue. The crude product was purified on a silica gel column eluting with chloroform:MeOH gradient. The fractions containing product were mixed and concentrated under vacuum. The residue was triturated with hexane to give 3-morpholino-5-nitropyridin-4-amine (LIII).

Workup

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto get a residue
  7. customThe crude product was purified on a silica gel column
  8. washeluting with chloroform
  9. additionThe fractions containing product
  10. additionwere mixed
  11. concentrationconcentrated under vacuum
  12. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-a840f538822e494a9dde57fde0d9d5d4
Source dataset
uspto-grants-2014_12
Patent number
US08901150B2

Reaction notes

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