Methanol → 6-Bromo-N-methyl-4-nitropyridin-3-amine

HRID 1907877Notes

Reaction equation

HRID 1907877 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH:11][CH3:12])=[CH:4][N+:3]=1[O-].P(Br)(Br)Br.O.CO>ClCCl>[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH:11][CH3:12])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24614Phosphorus tribromideHCID 866591292-Bromo-5-(methylamino)-4-nitropyridine 1-oxide

Product 1

HCID 866591306-Bromo-N-methyl-4-nitropyridin-3-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Bromo-5-(methylamino)-4-nitropyridine 1-oxide (10.0 g, 40.4 mmol) in 200 mL dichloromethane was mixed with phosphorous tribromide (10 mL, 106 mmol) in 50 mL dichloromethane at 10° C. and stirred for 10 minutes at ambient temperature. Water and methanol were added and the mixture was extracted with dichloromethane. The organic layers were washed with Na2CO3 (aq.) dried over MgSO4. The residue was triturated with ethanol, filtered and dried at 50° C. i. vac.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layers were washed with Na2CO3 (aq.)
  3. dry with materialdried over MgSO4
  4. customThe residue was triturated with ethanol
  5. filtrationfiltered
  6. customdried at 50° C. i

Sources & evidence

ORD record
ord-61cf86ea9cbb4b66b0127a2a0d12e471
Source dataset
uspto-grants-2013_12
Patent number
US08598190B2

Reaction notes

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