Trifluoroacetic acid → (4-Aminonaphthalen-1-yloxy)-acetonitrile

HRID 1171421Notes

Reaction equation

HRID 1171421 reaction equation
C(OC(=O)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]#[N:21])=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O.C(OCC)(=O)C>ClCCl>[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][C:20]#[N:21])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 59553417(4-Cyanomethoxynaphthalen-1-yl)-carbamic acid tert-butyl ester

Product 1

HCID 59553077(4-Aminonaphthalen-1-yloxy)-acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-cyanomethoxynaphthalen-1-yl)-carbamic acid tert-butyl ester (1.13 g, 3.8 mmol) in anhydrous dichloromethane (15 ml) at room temperature is added trifluoroacetic acid (5 ml). After 4 hours the mixture is poured into ethyl acetate (100 ml) and washed with saturated sodium bicarbonate solution (150 ml). The organic layer is then dried over anhydrous sodium sulfate and evaporated to dryness to give (4-aminonaphthalen-1-yloxy)-acetonitrile as a red brown solid.

Workup

  1. washwashed with saturated sodium bicarbonate solution (150 ml)
  2. dry with materialThe organic layer is then dried over anhydrous sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-941ea02db34d436094e3387ff9fdfad3
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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