Sodium Hydroxide → 8-Chloro-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 2389402Notes

Reaction equation

HRID 2389402 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:19])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[Cl:19][C:14]1[C:15]([O:17][CH3:18])=[CH:16][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH3:12])[C:9]=2[CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292769HCID 22292769, compound

Product 1

HCID 100366298-Chloro-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 109.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-trifluoroacetyl-8-chloro7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.399 g, 1.24 mmol) in methanol (20 mL) was treated with 15% aqueous NaOH (20 mL), and stirred overnight at 20 C. The product mixture was diluted with water (100 mL), extracted twice with EtOAc (100 mL), the combined organic phases were washed with brine (100 mL), dried with Na2SO4 and concentrated to give 0.306 g of a yellow solid. 1H NMR (400 MHz, CDCl3) d 7.05 (s, 1H), 6.59 (s, 1H), 3.80 (s, 3H), 3.0-2.8 (m, 6H), 2.62 (m, 1H), 2.16 (bs, 1H), 1.24 (d, J=7 Hz, 3H). MS calculated for C12H16ClNO+H: 226, observed: 226.

Workup

  1. extractionextracted twice with EtOAc (100 mL)
  2. washthe combined organic phases were washed with brine (100 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d9c02ed7afb48e485989f50f0254660
Source dataset
uspto-grants-2012_09
Patent number
US08273734B1

Reaction notes

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