Sodium Chloride → 2-Amino-4-(benzyloxy)-3-methoxybenzonitrile

HRID 339762Notes

Reaction equation

HRID 339762 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([N+:17]([O-])=O)[C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O.[Fe]>[NH2:17][C:11]1[C:10]([O:20][CH3:21])=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 582198454-(Benzyloxy)-3-methoxy-2-nitrobenzonitrile

Product 1

HCID 582198492-Amino-4-(benzyloxy)-3-methoxybenzonitrileYield 88%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A degassed solution of 4-(benzyloxy)-3-methoxy-2-nitrobenzonitrile (185 g, 651 mmol) in glacial acetic acid (3500 mL) and water (10 mL) was cooled to 5° C. and treated with iron powder (182 g, 3.25 mol). After 3 days the reaction mixture was filtered through Celite, and the filtrate concentrated under reduced pressure. The oil, thus obtained, was treated with a saturated sodium chloride solution, neutralized with a sodium bicarbonate solution and extracted into CH2Cl2. The resulting emulsion was filtered through Celite after which the organic layer was separated, washed with a saturated sodium chloride solution, dried (anh. sodium sulfate) and concentrated under reduced pressure to afford 2-amino-4-(benzyloxy)-3-methoxybenzonitrile as a solid (145 g, 88%): 1H NMR (DMSO-d6) δ: 7.32-7.44 (5H, m), 7.15 (1H, d), 6.47 (1H, d), 5.69 (2H, s), 5.15 (2H, s), 3.68 (3H, s).

Workup

  1. filtrationAfter 3 days the reaction mixture was filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe oil, thus obtained
  4. extractionextracted into CH2Cl2
  5. filtrationThe resulting emulsion was filtered through Celite after which the organic layer
  6. customwas separated
  7. washwashed with a saturated sodium chloride solution
  8. dry with materialdried (anh. sodium sulfate)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a1b2b97ece0420aa07a07c424b5d22f
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

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