Ammonium Chloride → HCID 90135712, compound

HRID 1506790Notes

Reaction equation

HRID 1506790 reaction equation
[CH3:1][C:2]1([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][N:13]=3)[CH:8]=2)[C:3]1=[O:21].[NH4+].[Cl-]>C(O)C.O.[Fe]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[C:3](=[O:21])[C:2]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([CH3:1])[CH2:11][CH2:10]3)=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90135630HCID 90135630, compound

Product 1

HCID 90135712HCID 90135712, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Iron powder (0.2 g, 3.58 mmol) was added to a solution of 3F (1.32 g, 3.58 mmol) in 10 mL of ethanol-water mixture (2:1) followed by NH4Cl (0.192 g, 3.58 mmol), and the mixture was refluxed for 3 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 and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography using 25% ethyl acetate in hexane to afford the title compound (1.01 g, 82%) as a solid. 1H NMR (300 MHz, DMSO-d6): δ 8.05 (d, J=2.7 Hz, 1H), 7.94-7.86 (m, 3H), 7.74 (d, J=8.5 Hz, 1H), 7.00 (dd, J1=2.8 Hz, J2=8.6 Hz, 1H), 5.67 (s, 2H), 4.00 (q, J=7.2 Hz, 2H), 3.18-2.88 (m, 2H), 2.82 (d, J=15.8 Hz, 1H), 2.48-2.26 (m, 2H), 1.90 (dt, J1=13.2 Hz, J2=4.5 Hz, 1H), 1.17 (s, 3H), 1.13 (t, J=6.9 Hz, 3H). ESI-MS m/z: 339 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 3 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 under reduced pressure
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c2769544a80946879102bab0376489fc
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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