Sodium Azide → 6-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

HRID 1487204Notes

Reaction equation

HRID 1487204 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13].[N-:14]=[N+]=[N-].[Na+]>>[CH3:1][O:2][C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][C:8](=[O:13])[NH:14][C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 366205-Methoxytetralone

Product 1

HCID 99423616-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-oneYield 75.5%

Procedure

To a solution of 5-methoxy-3,4-dihydronaphthalen-1(2H)-one (8.3 g, 47.15 mmol) in polyphosphoric acid (100 mL) was added sodium azide (3.6 g, 55.4 mmol) in small portions at 0° C. within 30 minutes. Then the mixture was slowly warmed to room temperature and stirred for another 16 hours, and then poured into ice-water. The precipitate was collected and dried to afford the product 6-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one as a white solid (6.8 g, yield 75.5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.48 (s, 1H), 7.13-7.17 (t, 1H, J=8.0 Hz), 6.77-6.79 (d, 1H, J=7.6 Hz), 6.58-6.60 (d, 1H, J=7.6 Hz), 3.78 (s, 3H), 2.68-2.72 (t, 2H, J=6.8 Hz), 2.11-2.14 (t, 2H, J=7.2 Hz), 1.99-2.05 (m, 2H).

Workup

  1. customThe precipitate was collected
  2. customdried

Sources & evidence

ORD record
ord-f3094850d80f476084d5e04fbb7eaf85
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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