Ammonia → HCID 86657418, compound

HRID 1191225Notes

Reaction equation

HRID 1191225 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[CH:5]=[C:4]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[N:3]=1.[NH3:20]>CO>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:20])[CH:5]=[C:4]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86657419HCID 86657419, compound

Product 1

HCID 86657418HCID 86657418, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2,4-Dichloro-6-(2,6-dichloro-phenyl)-3-nitro-pyridine (94.4 mg, 0.279 mmol, prepared as described in the previous step) was placed in a 8 mL vial equipped with a stir bar and dry MeOH (2 mL) was added via syringe. The resulting solution was gently heated with a heat gun to dissolve the solid and 7M NH3 in MeOH (2.00 mL, 14.0 mmol) was added via syringe. The resulting mixture was stirred at room temperature for 16 h and the solvent was removed under reduced pressure. The resulting residue was purified by preparative thin layer chromatography (TLC) on a 2000μ SiO2 plate developed with 1:4 EtOAc/heptane to yield 2-chloro-6-(2,6-dichlorophenyl)-3-nitropyridin-4-ylamine. 1H-NMR (400 MHz, CDCl3) δ: 7.33-7.45 (m, 2H), 7.27-7.33 (m, 1H), 6.68 (s, 1H), 5.86 (br. s., 2H). LCMS (ESI): Calculated for C11H6ClN3O2: 318.0 (M+H); Measured: 318.0.

Workup

  1. customvial equipped with a stir bar
  2. temperatureThe resulting solution was gently heated with a heat gun
  3. additionwas added via syringe
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified by preparative thin layer chromatography (TLC) on a 2000μ SiO2 plate

Sources & evidence

ORD record
ord-534d6bfee46c4658bf761fbd2fc9f904
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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