Acetic Acid → HCID 57435679, compound

HRID 558454Notes

Reaction equation

HRID 558454 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

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 9324935HCID 9324935, compound

Product 1

HCID 57435679HCID 57435679, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 mol) 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-water 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

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

Sources & evidence

ORD record
ord-260556410b2647e9af30f96f37cfadc4
Source dataset
uspto-grants-2011_11
Patent number
US08063056B2

Reaction notes

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