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

HRID 1376639Notes

Reaction equation

HRID 1376639 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 573710067-Methoxy-1-tetralone Oxime

Product 1

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

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. temperaturethe resulting suspension heated to ca. 80 C
  2. customyielding a black solid mixture
  3. temperatureThe residue was cooled
  4. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. concentrationthe combined organic layers were concentrated in vacuo
  6. customThe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-ae08097dd1ea485e803d268ffe27705d
Source dataset
uspto-grants-1997_09
Patent number
US05663166

Reaction notes

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