Hydrochloric Acid → HCID 178458442, compound

HRID 2046095Notes

Reaction equation

HRID 2046095 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12])[C:5]#[N:6].Cl.[NH2:15][OH:16].CCN(C(C)C)C(C)C>CCO>[OH:16][NH:15][C:5](=[NH:6])[C:4]1[CH:7]=[CH:8][C:9]([O:10][CH:11]([CH3:12])[CH3:13])=[C:2]([I:1])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 81531DiisopropylethylamineHCID 666150933-Iodo-4-isopropoxybenzonitrile

Product 1

HCID 178458442HCID 178458442, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 3-iodo-4-isopropoxybenzonitrile (0.576 g; 2 mmol), HCl×NH2OH (0.276 g; 4 mmol) and DIPEA (0.69 ml; 4 mmol) in EtOH (50 ml) was stirred for 18 h at 50° C. The solvent was distilled off and the residue was diluted to 50 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was distilled off to give the title product (0.61 g; 95%), as colourless solid. 1H-NMR (CDCl3) 8.0 (d, 1H, J=2.22 Hz); 7.55 (dd, 1H, J=9.54, 2.28 Hz); 6.77 (d, 1H, J=8.7 Hz); 4.95 (b, 2H); 4.69-4.63 (m, 1H); 1.42 (d, 6H).

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was diluted to 50 ml with EtOAc
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. distillationThe filtrate was distilled off

Sources & evidence

ORD record
ord-f21b5cc15f204e6a94e0b8558ef26885
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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