Ammonia → HCID 11346120, compound

HRID 2213811Notes

Reaction equation

HRID 2213811 reaction equation
[NH2-].[Na+].N.[Na].[CH2:5]([O:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH2:21][CH2:22][C:23]#[N:24])=[C:15](Br)[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[CH2:5]([O:12][C:13]1[CH:14]=[C:15]2[C:16]([CH2:21][CH:22]2[C:23]#[N:24])=[CH:17][C:18]=1[O:19][CH3:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 24533Sodium amideHCID 5360545SodiumHCID 11325431HCID 11325431, compound

Product 1

HCID 11346120HCID 11346120, compoundYield 66.1%

Conditions

Temperature
-33 °C

Procedure

A suspension of sodium amide is prepared from 100 mL of liquid ammonia, sodium (0.52 g, 22.8 mmol) and a catalytic amount of ferric nitrate. To this is added 3-(4-benzyloxy-2-bromo-5-methoxyphenyl)-propionitrile (2 g, 5.7 mmol) in portions and the reaction stirred at −33° C. 45 minutes. The reaction then cooled down to −78° C. and quenched with ammonium chloride. The liquid ammonia is allowed to evaporate and the resulting solid residue is washed with water. The tan solid obtained is purified by flash chromatography, using 4:1 hexanes/ethyl acetate as an eluent. The clean fractions are combined and reduced in vacuo to yield 1 g of 4-benzyloxy-3-methoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile as a clear oil that solidified into a white solid upon standing, mp 85° C.

Workup

  1. custom45 minutes
  2. customThe reaction
  3. temperaturethen cooled down to −78° C.
  4. customquenched with ammonium chloride
  5. customto evaporate
  6. washthe resulting solid residue is washed with water
  7. customThe tan solid obtained
  8. customis purified by flash chromatography

Sources & evidence

ORD record
ord-794c33f9a3e6485a9363867e61620162
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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