Triethylamine → 2-(7-Methoxynaphthalen-1-yl)acetonitrile

HRID 483393Notes

Reaction equation

HRID 483393 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]([NH2:16])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]#[N:16])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 151491272-(7-Methoxynaphthalen-1-yl)acetamide

Product 1

HCID 112640682-(7-Methoxynaphthalen-1-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (7-methoxynaphth-1-yl)acetamide obtained in Stage E is suspended in 80 ml of anhydrous THF, and triethylamine is added. The solution is cooled in an ice bath, and then trifluoroacetic anhydride is added dropwise with magnetic agitation. Agitation is continued for one hour at room temperature. Then the mixture is dried and the residue taken up in water. The precipitate which forms is spun down, dried and recrystallized in isopropyl ether.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. customThen the mixture is dried
  3. customdried
  4. customrecrystallized in isopropyl ether

Sources & evidence

ORD record
ord-0d8297132e0147d980039df82d6e1541
Source dataset
uspto-grants-1993_07
Patent number
US05225442

Reaction notes

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