Sodium Carbonate → 5-Methyl-4,5-dihydro-1h-1-benzazepin-2(3h)-one

HRID 1034457Notes

Reaction equation

HRID 1034457 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[N:12]O)[CH2:4][CH2:3]1.C(=O)([O-])[O-:15].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][CH:2]1[C:11]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:5](=[O:15])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 58794254HCID 58794254, compound

Product 1

HCID 131733325-Methyl-4,5-dihydro-1h-1-benzazepin-2(3h)-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 800 mg (4.57 mmol) of 4-methyl-1-tetralone oxime and 4.0 g of polyphosphoric acid was heated at 120° C. in an oil bath for 20 minutes. The dark brown mixture was cooled to 80° C. and poured into ice water. The solution was neutralized by the addition of 10% aqueous sodium carbonate then extracted chloroform (3×50 mL). The combined extracts were washed with water, dried over magnesium sulfate and filtered. Evaporation of the solvent followed by column chromatography on silica gave the product as an off-white solid (670 mg, 84%). 1H NMR (200 MHz, CDCl3): 1.30 (d, 8 Hz, 3H), 1.68 (m, 1H), 2.30 (m, 3H), 3.11 (m, 1H), 6.98 (m, 1H), 7.15-7.30 (m, 3H), 8.55 (br s, 1H). 13C NMR: 18.22, 32.89, 32.98, 37.28, 121.95, 125.67, 125.93, 126.98, 137.69, 137.80, 176.04.

Workup

  1. temperatureThe dark brown mixture was cooled to 80° C.
  2. washThe combined extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-db4c15b62c4046538dd05cb75ba38219
Source dataset
uspto-grants-1994_05
Patent number
US05317017

Reaction notes

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