Ammonia → HCID 11346120, compound

HRID 902407Notes

Reaction equation

HRID 902407 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 is stirred at −33° C. for 45 minutes. The reaction is 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 solidifies into a white solid upon standing, mp 85° C.

Workup

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

Sources & evidence

ORD record
ord-0d90afd563b543fdbae67f8aacf6e7bd
Source dataset
uspto-grants-2008_04
Patent number
US07365197B2

Reaction notes

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