Acetic Acid → HCID 57435679, compound

HRID 249739Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:10]2)=[O:5].C(O)(=O)C.[Br:20]Br>O>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[Br:20])[CH2:12][CH2:11][CH2:10]2)=[O:5]

Participants

Conditions

Temperature: -10 °C

Procedure

A mixture of 5-methoxyacetamidoindan (5.50 g, 0.027 mol) and glacial acetic acid (25 ml) was cooled in an ice-water bath (−10° C.). Bromine (1.5 ml, 0.029 mmol) was then dropwise added over a 20 min period while the temperature was kept between 10-15° C. The reaction mixture was then stirred for a longer 1 hour and then it was poured into an ice-wafer bath (100 ml) with the aid of water (70 ml). The precipitate was collected by filtration, washed with plenty of water (150 ml) and dried in vacuo over P2O5 to afford the title compound (6.98 g, 91%), m.p. 84-86° C.; 1H-NMR (250 MHz, CDCl3, TMS) 2.09 (m, 2H, 2-CH2), 2.88 (m, 4H, 1-CH2 and 3-CH2), 3.55 (s, 3H, OCH3), 4.04 (s, 2H, 2-CH2OMe), 7.34, 8.22 (2×s, 2H, 4-H, 7-H), 8.83 (s, 1H, CONH);

Workup

customwas kept between 10-15° C
filtrationThe precipitate was collected by filtration
washwashed with plenty of water (150 ml)
dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record: ord-f3b9741f81ca49dcab26dfca0972e777
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863284B2

Reaction notes

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