Trichloroacetic Acid → 8-Methoxy-2,3,4,5-tetrahydro-benzo[c]azepin-1-one

HRID 865334Notes

Reaction equation

HRID 865334 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[N:13]O)=[CH:5][CH:4]=1.ClC(Cl)(Cl)C(O)=[O:18]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][NH:13][C:10](=[O:18])[C:11]=2[CH:12]=1

Participants

3

Reactant 2

HCID 6421Trichloroacetic AcidHCID 57371006HCID 57371006, compound

Product 1

HCID 112755298-Methoxy-2,3,4,5-tetrahydro-benzo[c]azepin-1-oneYield 22.3%

Conditions

Temperature
80 °C

Procedure

Following a procedure of Tomita, et. al., J. Chem. Soc. C 1969, 183, 7-methoxytetralone oxime (45.0 g, 0.235 mol) was mixed with solid trichloroacetic acid (150 g), and the resulting suspension heated to ca. 80° C., at which time a violent exotherm ensued, yielding a black solid mixture. The residue was cooled, partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution, and the combined organic layers were concentrated in vacuo. The residue was purified by chromatography over silica gel to yield 10.0 g (22%) of 8-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one. An analytical sample was obtained by recrystallization from CH2Cl2 /hexanes to yield colorless crystals: mp. 99°-101° C. (lit. (see above) 100°-101° C.); 1H NMR (CDCl3) d7.35(brs, 1H), 7.30(d, J=3 Hz, 1H), 7.10(d, J=9 Hz, 1H), 6.95(dd, J=3, 9 Hz, 1H), 3.82(s, 3H), 3.10(q, J=6 Hz, 2H), 2.80(t, J=6 Hz, 2H), 1.98(m, 2H).

Workup

  1. customyielding a black solid mixture
  2. temperatureThe residue was cooled
  3. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. concentrationthe combined organic layers were concentrated in vacuo
  5. customThe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-7a9a7c49b62948488e3e3a30820ded4f
Source dataset
uspto-grants-1996_10
Patent number
US05565449

Reaction notes

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