Hydrochloric Acid → 2-Amino-1-(4-bromophenyl)ethanone

HRID 535117Notes

Reaction equation

HRID 535117 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].C1N2CN3CN(C2)C[N:13]1C3.Cl>C1(C)C=CC=CC=1.C(O)C>[NH2:13][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 74544-Bromophenacyl bromide

Product 1

HCID 216392-Amino-1-(4-bromophenyl)ethanoneYield 92.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 2-bromo-1-(4-bromophenyl)ethanone (130 g 0.478 mol) in toluene (2500 mL) was added hexamethylenetetramine (65.6 g 0.478 mol). The mixture was stirred at 40° C. for 16 hrs. The resulting solid was filtered off and washed with toluene and ether to give a white solid. To a stirred suspension of this white solid in ethanol (800 mL) was added concentrated hydrochloride acid (300 mL). The mixture was stirred at ambient temperature for 20 hrs. The solid was collected by filtration and washed with ethanol and water and dried in vacuo to give 2-amino-1-(4-bromophenyl)ethanone (4) (95 g, yield: 92%) as a white solid, which was used without purification for the next step. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.58 (s, br, 2H), 7.96 (d, J=8.7 Hz, 2H), 7.81 (d, J=8.7 Hz, 2H), 4.48-4.52 (m, 2H). ES LC-MS m/z=214, 216 (M+H)+.

Workup

  1. filtrationThe resulting solid was filtered off
  2. washwashed with toluene and ether
  3. customto give a white solid
  4. stirringThe mixture was stirred at ambient temperature for 20 hrs
  5. filtrationThe solid was collected by filtration
  6. washwashed with ethanol and water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-09dfe5d068ae4598950f0c33ab7eefb0
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

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