Ammonia → HCID 67434521, compound

HRID 2036629Notes

Reaction equation

HRID 2036629 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]([N+:16]([O-])=O)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.N>CCO>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 67432130HCID 67432130, compound

Product 1

HCID 67434521HCID 67434521, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (3,5-difluorophenyl)-(2-nitro-pyridin-3-yl)-amine (900 mg, 3.58 mmol) in EtOH (10.7 mL) was added stannous chloride dihydrate (3.23 g, 14.33 mmol) and 35% HCl (0.5 mL). The reaction mixture was stirred at 75° C. for 2 h, when it was basified using aqueous ammonia and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated in vacuo to provide N3-(3,5-Difluorophenyl)-pyridine-2,3-diamine: 1H NMR (400 MHz, DMSO-d6) δ 5.703 (br s, 2H), 6.227-6.289 (m, 2H), 6.383-6.442 (m, 1H), 6.564-6.595 (m, 1H), 7.333 (dd, J=1.6 Hz, J=1.6 Hz, 1H), 7.784-7.791 (m, 2H); LC-MS (ESI) m/z 222.0 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1794e6addf4643a69c102b9bb29633ab
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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