Ammonium Chloride → 1,2-Dihydro-3,4-dimethoxybenzocyclobutene-1-carbonitrile
Reaction equation
Br[C:2]1[C:7]([CH2:8][CH2:9][C:10]#[N:11])=[C:6]([O:12][CH3:13])[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1.[NH4+].[Cl-]>N>[CH3:13][O:12][C:6]1[C:7]2[CH2:8][CH:9]([C:10]#[N:11])[C:2]=2[CH:3]=[CH:4][C:5]=1[O:14][CH3:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
A mixture of liquid NH3 (400 mL) and catalytic Fe(NO3)3 was stirred under N2 at -50° C. A small portion of Na metal (from a total amount of 20 g., 0.87 mole) was added. Air was bubbled through the reaction mixture briefly until a black precipitate appeared. The remaining Na was added portionwise. 3-(6-bromo-2,3-dimethoxyphenyl)-propionitrile (31.1 g, 0.115 mole) was added over 70 minutes as the reaction mixture was stirred at slow reflux. When the addition was complete, the reaction mixture was stirred at reflux for 1/2 hr, then was cooled to -55° C. as NH4Cl (35.2 g, 0.66 mole) was added slowly. NH3 was allowed to evaporate overnight. Water was added cautiously with stirring. The solid was filtered, washed with water, dried (in-vacuo) to yield 21.0 g gray powder, (97%); M+ 189.
Workup
- addition, 0.87 mole) was added
- customAir was bubbled through the reaction mixture briefly until a black precipitate
- additionThe remaining Na was added portionwise
- stirringwas stirred at slow reflux
- additionWhen the addition
- stirringthe reaction mixture was stirred
- temperatureat reflux for 1/2 hr
- additionwas added slowly
- customto evaporate overnight
- additionWater was added cautiously
- stirringwith stirring
- filtrationThe solid was filtered
- washwashed with water
- customdried (in-vacuo)
Sources & evidence
- ORD record
- ord-c610de19a56740d2a40bf5b51b514479
- Source dataset
- uspto-grants-1986_10
- Patent number
- US04618683
Reaction notes
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