Ethyl Acetate → (4-Cyanomethoxynaphthalen-1-yl)-carbamic acid tert-butyl ester

HRID 1171420Notes

Reaction equation

HRID 1171420 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]#[N:29].C(OCC)(=O)C>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19][CH2:27][C:28]#[N:29])=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 59553417(4-Cyanomethoxynaphthalen-1-yl)-carbamic acid tert-butyl esterYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-tertbutyloxycarbonyl-4-amino-1-naphthol (1.0 g, 3.86 mmol), potassium carbonate (1.06 g, 7.7 mmol) and bromoacetonitrile (0.4 ml, 5.8 mmol) in anhydrous dimethylformamide (10 ml) are stirred at room temperature for 5 hours. The mixture is poured into ethyl acetate (100 ml) and washed with water (2×100 ml). The organic layer is then dried over anhydrous sodium sulfate and evaporated to dryness to give (4-cyanomethoxynaphthalen-1-yl)-carbamic acid tert-butyl ester as a red brown solid (1.132 g). 1H NMR 300 MHz (CDCl3) 8.2 (d, 1H, J=11.5 Hz), 7.85 (d, 1H, J=111.5 Hz), 7.55-7.75 (m, 3H), 6.9 (d, 1H, J=14 Hz), 6.62 (s, 1H), 4.95 (s, 2H), 1.5 (s, 9H).

Workup

  1. washwashed with water (2×100 ml)
  2. dry with materialThe organic layer is then dried over anhydrous sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-ff84b4c245b74e769348957c34916a80
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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