3'-Aminoacetophenone → HCID 52984174, compound

HRID 529859Notes

Reaction equation

HRID 529859 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1)=[O:3].C(N(CC)CC)C.[Br:18][CH:19]([CH3:23])[C:20](Br)=[O:21]>CN(C)C=O.O>[C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:20](=[O:21])[CH:19]([Br:18])[CH3:23])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 3

HCID 74173'-AminoacetophenoneHCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 52984174HCID 52984174, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-amino acetophenone (1.0 g, 7.35 mmol) in dimethylformamide (DMF) (10.0 mL) was added triethylamine (Et3N) (1.11 g, 11.03 mmol) at 0° C. followed by the slow addition of 2-bromopropionyl bromide (1.75 g, 8.08 mmol). The reaction was stirred at room temperature (rt) under N2 atmosphere for 3 h, diluted with water (50.0 mL) and the precipitated pale brown solid was filtered and dried to give the title product in 80% yield. 1H NMR (CDCl3, 400 MHz): 8.47 (br s, NH), 8.09-8.08 (m, 1H), 7.92 (dd, J=8.0 Hz, J=1.2 Hz, 1H), 7.73 (dd, J=8.0 Hz, J=1.2 Hz, 1H), 7.46 (t, J=8.0 Hz, 1H), 4.60 (q, J=6.8 Hz, 1H), 2.62 (s, 3H), 1.96 (d, J=7.2 Hz, 3H). 13C NMR (CDCl3, 100 MHz): 198.0, 167.8, 137.8, 137.7, 129.5, 124.8, 124.6, 119.5, 44.8, 26.7, 22.7. ESI-MS calcd for C11H12BrNO2 (M+Na)+291.99. found 292.0.

Workup

  1. filtrationthe precipitated pale brown solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-1b4da2033cca45a094194008b2a5cc48
Source dataset
uspto-grants-2016_05
Patent number
US09347948B2

Reaction notes

Loading…