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

HRID 2383404Notes

Reaction equation

HRID 2383404 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)acetamideYield 79.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-amino-3,4-dihydronaphthalen-1(2H)-one (0.5 g, 3.1 mmol) in pyridine (5 mL) was added acetic anhydride (0.38 g, 3.7 mmol). The solution was stirred at room temperature for 3 hours. The reaction was then diluted with dichloromethane (50 mL). The organic layer was separated, washed with 2M HCl (2×25 mL), brine (50 mL), dried using sodium sulfate and concentrated under reduced pressure. The crude was product was obtained as an off colored solid (0.5 g, 79%) and used in the next reaction without any further purification. 1H NMR (CDCl3, 400 MHz): δ 8.94 (d, J=8.0 Hz, 1H), 7.72 (s, 1H), 7.62 (s, 1H), 7.20 (d, J=8.0 Hz, 1H0, 2.96 (t, J=6.2 Hz, 2H), 2.62 (quintet, J=6.0 Hz, 2H), 2.12 (s, 3H), 2.11 (t, J=6.0 Hz, 2H); LCMS [M+H]: 204.

Workup

  1. customThe organic layer was separated
  2. washwashed with 2M HCl (2×25 mL), brine (50 mL)
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd2ee174d164400ab75aade6f4da1404
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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