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

HRID 130800Notes

Reaction equation

HRID 130800 reaction equation
Cl.CO[CH:4](OC)[CH2:5][N:6]([CH3:18])[C:7](=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1>CC(O)=O.ClCCl>[CH3:16][O:15][C:11]1[CH:12]=[CH:13][C:14]2[CH:4]=[CH:5][N:6]([CH3:18])[C:7](=[O:17])[CH2:8][C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59730089N-(2,2-dimethoxyethyl)-2-(3-methoxyphenyl)-N-methylacetamide

Product 1

HCID 597302948-methoxy-3-methyl-2,3-dihydro-1H-3-benzazepin-2-oneYield 84%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Add concentrated HCl (3.5 L) to a solution of N-(2,2-dimethoxyethyl)-2-(3-methoxyphenyl)-N-methylacetamide (790 g, 2.709 mol, 1.0 eq) dissolved in HOAc (3.5 L). Stir the mixture for 16 hours at room temperature. Dilute the reaction mixture with 4 L of dichloromethane and then quench slowly with 50% NaOH (4.0 L) over 2 hours. Separate the two layers. Collect the organic layer, dry over sodium sulfate and concentrate under vacuum to yield an off-white solid. The solid is put through a silica plug (1/1 hexanes/ethyl acetate) to obtain the product (Cmpd N, 460 g, 84% yield).

Workup

  1. customquench slowly with 50% NaOH (4.0 L) over 2 hours
  2. customSeparate the two layers
  3. customCollect the organic layer
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate under vacuum
  6. customto yield an off-white solid
  7. customto obtain the product (Cmpd N, 460 g, 84% yield)

Sources & evidence

ORD record
ord-92f8b78365cd4da1b2b07fc3f2606ecb
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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