N-methyl-2-pyrrolidone → HCID 54209923, compound

HRID 1789002Notes

Reaction equation

HRID 1789002 reaction equation
Br[C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH:4]=[CH:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[OH:15].[CH3:20][N:21]1CCCC1=O>>[C:20]([C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH:4]=[CH:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[OH:15])#[N:21]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 53712388HCID 53712388, compound

Product 1

HCID 54209923HCID 54209923, compoundYield 39%

Procedure

Cuprous cyanide (1.03 g; 11.5 mM) and 2-(o-bromocinnamyl)-4-methoxyphenol (1.03 g; 3.23 mM) were combined in 12 ml of anhydrous N-methylpyrrolidinone. Nitrogen was bubbled through the resulting suspension for five minutes and it was then heated to 175° under positive nitrogen pressure for 2 hours. The reaction was poured into 50 ml of conc. NH4OH and 50 ml of water. The emulsion was extracted three times with ether and the ether extracts were washed once with water. Drying over magnesium sulfate was followed by solvent removal leaving a brown oil. This crude product was purified by flash chromatography with 35% ethyl acetate in hexane on a 30 mm×6" column of silica gel. Recrystallization from ethyl acetate/hexane gave 2-(o-cyanocinnamyl)-4-methoxyphenol as a tan solid (335 mg, 39% yield) m.p. 72-74°.

Workup

  1. customNitrogen was bubbled through the resulting suspension for five minutes
  2. temperatureit was then heated to 175° under positive nitrogen pressure for 2 hours
  3. additionThe reaction was poured into 50 ml of conc. NH4OH and 50 ml of water
  4. extractionThe emulsion was extracted three times with ether
  5. washthe ether extracts were washed once with water
  6. dry with materialDrying over magnesium sulfate
  7. customwas followed by solvent removal
  8. customleaving a brown oil
  9. customThis crude product was purified by flash chromatography with 35% ethyl acetate in hexane on a 30 mm×6" column of silica gel
  10. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-db6c62ed346343019f2747bac432b479
Source dataset
uspto-grants-1987_08
Patent number
US04686235

Reaction notes

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