Hydrochloric Acid → HCID 22136223, compound

HRID 711717Notes

Reaction equation

HRID 711717 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]=1[C:6]#[N:7])([O-])=O.Cl>CO.[Fe]>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67397106HCID 67397106, compound

Product 1

HCID 22136223HCID 22136223, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-6-(phenoxy)benzonitrile (Example 113c) (1.94 g, 8.08 mmol) in MeOH (164 mL) was slowly added concentrated HCl (7.23 mL) followed by iron powder (1.58 g, 28.3 mmol). The reaction was refluxed for 30 min and concentrated in vacuo. The residue was dissolved in EtOAc and washed with 1N NaOH, water and brine. The organic layer was dried over MgSO4, filtered, concentrated and purified by flash chromatography 1:1 Hexane:EtOAc to yield 2-amino-6-phenoxybenzonitrile (384 mg, 22.6%). 1H NMR (400 MHz, MeOD) δ 5.97 (d, J=8.3 Hz, 1H), 6.50 (d, J=8.6 Hz, 1H), 7.06 (m, 2H), 7.18 (m, 2H), 7.40 (m, 2H). MS 210 (MH+).

Workup

  1. temperatureThe reaction was refluxed for 30 min
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 1N NaOH, water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography 1:1 Hexane

Sources & evidence

ORD record
ord-26783c9eb05d46a1954b7bb8404873dd
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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