Acetic Anhydride → N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

HRID 2089477Notes

Reaction equation

HRID 2089477 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1.ClCCl>[O:12]=[C:8]1[CH2:7][CH2:6][CH2:5][C:4]2[CH:3]=[C:2]([NH:1][C:13](=[O:15])[CH3:14])[CH:11]=[CH:10][C:9]1=2

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-amino-3,4-dihydro-2H-naphthalen-1-one (CAS#3470-53-9, 0.875 g, 5.44 mmol) in pyridine (5 mL) is added acetic anhydride (0.83 g, 8.16 mmol). After 1 hour, the solution is diluted with dichloromethane and washed with water and 1M aqueous HCl. The organic phase is dried over sodium sulfate, filtered, and concentrated to give N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide; 1H NMR (400 MHz, CDCl3) δ ppm 2.09-2.16 (m, 2 H), 2.22 (s, 3 H), 2.59-2.67 (m, 2 H), 2.95 (t, J=6.1 Hz, 2 H), 7.21 (dd, J=8.3, 2.1 Hz, 1 H), 7.42 (br. s., 1 H), 7.70 (br. s., 1 H), 8.00 (d, J=8.3 Hz, 1 H).

Workup

  1. washwashed with water and 1M aqueous HCl
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-637e5e08f5e2483b993a2e70ed183158
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

Loading…