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

HRID 1259496Notes

Reaction equation

HRID 1259496 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.C(=O)(O)[O-].[Na+]>C(O)(=O)C.O.[Cl-].[Na+].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 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

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 brine, neutralized with a sodium bicarbonate solution and extracted into DCM. The resulting emulsion was filtered through Celite after which the organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated under reduced pressure to afford the title compound 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 DCM
  5. filtrationThe resulting emulsion was filtered through Celite after which the organic layer
  6. customwas separated
  7. washwashed with brine
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3127113d63ec40649fd2ef0f36c1415e
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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