Acetone → HCID 66747234, compound

HRID 711793Notes

Reaction equation

HRID 711793 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 stirred 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-66cd3a2331774f0cb34582483d051251
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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