Acetone → HCID 66747234, compound

HRID 471655Notes

Reaction equation

HRID 471655 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16](OC)[CH:15]=2)[C:5]=1[C:6]#[N:7])([O-])=O.CC(C)=O.[Cl-].[NH4+]>[Zn].O>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]=1[C:6]#[N:7]

Participants

6

Reactant 3

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 66746419HCID 66746419, compound

Product 1

HCID 66747234HCID 66747234, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

To a mixture of 2-nitro-6-(3-methoxybenzyloxy)benzonitrile (Example 193c) (480 mg, 1.69 mmol) in 5:1 acetone:water (9 mL) was added zinc (552 mg, 8.44 mmol) and ammonium chloride (911 mg, 16.9 mmol). The reaction was stiffed at room temperature for 30 minutes, then filtered and concentrated. The residue was purified by flash chromatography (55:45 EtOAc:Hexane) to provide 2-amino-6-(benzyloxy)benzonitrile (337 mg, 78%). 1H NMR (400 MHz, d-DMSO) δ 3.73 (s, 3H), 5.04 (s, 1H), 6.27 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.4 Hz, 1H), 7.06-6.97 (m, 3H), 7.27 (t, J=8.0 Hz, 1H), 7.36 (s, 1H), 7.55 (s, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (55:45 EtOAc:Hexane)

Sources & evidence

ORD record
ord-dc41923c077f463f99f1b3219ef920e7
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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