Ammonium Chloride → HCID 90152012, compound

HRID 1506786Notes

Reaction equation

HRID 1506786 reaction equation
[NH4+].[Cl-].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18](=[O:22])[C:17]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH2:23][C:24]([F:27])([F:26])[F:25])[CH2:16][CH2:15]3)=[N:10][CH:11]=1)([O-])=O>C(O)C.O.[Fe]>[NH2:3][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18](=[O:22])[C:17]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH2:23][C:24]([F:27])([F:25])[F:26])[CH2:16][CH2:15]3)=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90152013HCID 90152013, compound

Product 1

HCID 90152012HCID 90152012, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Iron powder (0.218 g, 3.9 mmol) and NH4Cl (0.208 g, 3.9 mmol) was added to a solution of 1I (1.7 g, 3.9 mmol) in 15 mL of ethanol-water (2:1) mixture. The reaction mixture was refluxed for 3 h, and solvent was removed under reduced pressure. The crude product was purified by flash chromatography using 25% ethyl acetate in hexane to afford the title compound (1.2 g, 53%) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=2.8 Hz, 1H), 8.09 (d, J=8.2 Hz, 1H), 7.88-7.78 (m, 2H), 7.60 (d, J=8.4 Hz, 1H), 7.06 (dd, J1=2.9 Hz, J2=8.5 Hz, 1H), 4.13 (q, J=7.2 Hz, 2H), 3.86 (s, 2H), 3.20-3.02 (m, 2H), 2.98-2.81 (m, 2H), 2.72-2.53 (m, 2H), 2.51-2.28 (m, 2H), 1.24 (t, J=7.6 Hz, 3H). ESI-MS m/z: 407 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customsolvent was removed under reduced pressure
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c715d3689922498b8f11ada637efe6f3
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

Loading…