Ethanol → HCID 90067262, compound

HRID 929159Notes

Reaction equation

HRID 929159 reaction equation
[Cl-].[NH4+].[C:3]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([NH2:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=2[Cl:19])=[CH:5][CH:4]=1.C(O)C>O.[Fe]>[C:3]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([NH2:15])[C:12]([NH2:16])=[CH:11][C:10]=2[Cl:19])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 118413244HCID 118413244, compound

Product 1

HCID 90067262HCID 90067262, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Ammonium chloride (632 mg, 11.82 mmol) and iron (1320 mg, 23.64 mmol) were added to a stirred mixture of 6-([1,1′-biphenyl]-4-yl)-5-chloro-3-nitropyridin-2-amine (550 mg, 1.688 mmol) in water (2 ml)/Ethanol (2 mL) and the mixture was stirred at 60° C. for 3 h. The mixture was filtered through Celite™, rinsing with ethyl acetate (100 mL). Water (80 mL) was added and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic fractions were washed with brine (saturated, 80 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel Biotage™ 40S, eluting with 0-60% EtOAc/hexane to give title compound. LC-MS: calculated for C17H14ClN3 295.09 observed m/e: 296.12 (M+H)+ (Rt 1.09/2 min).

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. washrinsing with ethyl acetate (100 mL)
  3. additionWater (80 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic fractions were washed with brine (saturated, 80 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe resulting residue was purified by column chromatography on silica gel Biotage™ 40S
  10. washeluting with 0-60% EtOAc/hexane

Sources & evidence

ORD record
ord-9fcae879a4be4781a57c4d75d7d64b7f
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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