Hydrochloric Acid → 8-methoxy-2,3-dihydro-1H-3-benzazepin-2-one

HRID 1040736Notes

Reaction equation

HRID 1040736 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1.Cl>C(O)(=O)C>[CH3:15][O:14][C:10]1[CH:11]=[CH:12][C:13]2[CH:3]=[CH:4][NH:5][C:6](=[O:16])[CH2:7][C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13853346n-(2,2-Dimethoxyethyl)-2-(3-methoxyphenyl)acetamide

Product 1

HCID 42200938-methoxy-2,3-dihydro-1H-3-benzazepin-2-oneYield 51.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(2,2-dimethoxy-ethyl)-2-(3-methoxy-phenyl)-acetamide (53.6 g, 0.21 mol) in acetic acid (140 mL) and aqueous 37% HCl (100 mL) was stirred at room temperature overnight. The reaction mixture was diluted with a ice/water mixture with vigorous stirring to yield a precipitate. The precipitate was filtered, rinsed with water, and then dissolved in dichloromethane, dried (MgSO4), concentrated and dried in high vacuum to give 8-methoxy-1,3-dihydrobenzo[d]azepin-2-one (20.5 g, 51%) as a tan solid. 1H-NMR (CDCl3) δ 8.23 (br s, 1H), 7.15 (d, J=8.3 Hz, 1H), 6.86 (d, J=8.6 Hz, 1H), 6.79, (s, 1H), 6.33 (d, J=9.1 Hz, 1H), 6.16 (dd, J=4.8, 9.3 Hz, 1H), 3.83 (s, 3H), 3.48 (s, 2H); LC/MS (ESI+): 190.05 (M+H).

Workup

  1. customto yield a precipitate
  2. filtrationThe precipitate was filtered
  3. washrinsed with water
  4. dissolutiondissolved in dichloromethane
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customdried in high vacuum

Sources & evidence

ORD record
ord-e8840690ef154c19b24e2e097670193e
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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