Ammonium Chloride → HCID 90135536, compound

HRID 1506796Notes

Reaction equation

HRID 1506796 reaction equation
[CH2:1]([C:3]1([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][N:14]=3)[CH:9]=2)[C:4]1=[O:22])[CH3:2].[NH4+].[Cl-]>C(O)C.O.[Fe]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[C:4](=[O:22])[C:3]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH2:1][CH3:2])[CH2:12][CH2:11]3)=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90135473HCID 90135473, compound

Product 1

HCID 90135536HCID 90135536, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Iron powder (1.533 g, 27.5 mmol) was added to a solution of 4F (2.1 g, 5.49 mmol) in 30 mL of ethanol-water mixture (5:1) followed by NH4Cl (0.015 g, 0.275 mmol), and the mixture was refluxed for 5 h. The solvent was removed under reduced pressure, and residue was partitioned between ethyl acetate and water. The separated organic layer was dried over sodium sulfate, filtered, and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography using 40% ethyl acetate in hexane to afford the title compound (1.65 g, 85%) as a solid. 1H NMR (300 MHz, CDCl3): δ 8.20 (d, J=2.7 Hz, 1H), 8.11 (d, J=7.5 Hz, 1H), 7.82 (s, 1H), 7.78 (d, J=8.4 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.06 (dd, J1=2.7 Hz, J2=8.4 Hz, 1H), 4.11 (q, J=5.7 Hz, 2H), 3.84 (bs, 2H), 3.23-3.12 (m, 1H), 3.06-2.93 (m, 2H), 2.56-2.46 (m, 2H), 2.14-2.07 (m, 1H), 1.85-1.61 (m, 2H), 1.24 (t, J=6.9 Hz, 3H), 0.92 (t, J=7.8 Hz, 3H). ESI-MS m/z=353 (M+H).

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. customThe solvent was removed under reduced pressure, and residue
  3. customwas partitioned between ethyl acetate and water
  4. dry with materialThe separated organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-092c479dc2354698bcddec525ad62626
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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