Water → HCID 118046519, compound

HRID 595838Notes

Reaction equation

HRID 595838 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:5]=[N:6][C:7]=1[N+:8]([O-])=O.O.Cl[Sn]Cl>CCO.C(Cl)Cl>[Br:1][C:2]1[C:7]([NH2:8])=[N:6][CH:5]=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 66664889HCID 66664889, compound

Product 1

HCID 118046519HCID 118046519, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

4-(5-Bromo-6-nitropyridin-3-yl)morpholine (95 mg, 0.33 mmol) was dissolved in EtOH (12 mL) and water (3.0 mL) was added, followed by SnCl2 (313 mg, 1.65 mmol). The reaction mixture was heated to 80° C. for 2 h, cooled to room temperature and diluted with DCM. The two phases were separated, the organic phase was washed with water. The water phase was back extracted with DCM. The pH was adjusted to 12 with 6N NaOH and the mixture was further extracted with DCM. The organic extracts were combined, dried (Na2SO4) and evaporated under reduced pressure obtaining the desired 3-bromo-5-morpholinopyridin-2-amine (71.5 mg, 84%). LCMS (m/z): 260.0 (MH+), 0.37 min.

Workup

  1. temperaturecooled to room temperature
  2. customThe two phases were separated
  3. washthe organic phase was washed with water
  4. extractionThe water phase was back extracted with DCM
  5. extractionthe mixture was further extracted with DCM
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0c6eeba0776e421ba19cd3eb1e67241e
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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