Ammonium Chloride → HCID 123552372, compound

HRID 2202691Notes

Reaction equation

HRID 2202691 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]([O:17][Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20])[CH2:13][N+:14]([O-])=O)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Cl-].[NH4+]>CCO.O.[Fe]>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]([O:17][Si:18]([CH2:19][CH3:20])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:13][NH2:14])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 123278338HCID 123278338, compound

Product 1

HCID 123552372HCID 123552372, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a clear yellow solution of 3-chloro-4-(2-nitro-1-((triethylsilyl)oxy)ethyl)quinoline (0.511 g, 1.39 mmol) in EtOH (7.96 mL) and water (1.99 mL) at room temperature was added iron powder (0.778 g, 13.9 mmol) and ammonium chloride (0.745 g, 13.9 mmol). The dark brown mixture was stirred and heated at 60° C. After 4 h, the mixture was cooled to room temperature and filtered through a celite pad and washed the pad with MeOH (3×30 mL). The combined filtrates were concentrated in vacuo. The residue was partitioned between EtOAc (100 mL) and water (50 mL). The mixture (pH ˜4.0) washed with saturated aqueous NaHCO3 (1×50 mL), water (1×50 mL), and brine (1×50 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and dried under high vacuum to give 2-(3-chloroquinolin-4-yl)-2-((triethylsilyl)oxy)ethanamine (A275-6) as a yellow syrup. 1H NMR (400 MHz, DMSO-d6) δ 8.84 (1H, s), 8.72 (1H, d, J=8.2 Hz), 8.04 (1H, dd, J=8.4, 1.0 Hz), 7.76 (1H, ddd, J=8.4, 6.9, 1.4 Hz), 7.64 (1H, ddd, J=8.5, 7.0, 1.3 Hz), 5.52 (1H, dd, J=7.6, 5.5 Hz), 3.16 (1H, dd, J=13.0, 7.9 Hz), 2.88 (1H, dd, J=13.0, 5.4 Hz), 1.74 (1H, br. s.), 0.71-0.80 (1H, m), 0.71-0.80 (9H, m), 0.37-0.57 (6H, m); LCMS (ESI) m/z 337.1 (M+H)+.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationfiltered through a celite pad
  3. washwashed the pad with MeOH (3×30 mL)
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. customThe residue was partitioned between EtOAc (100 mL) and water (50 mL)
  6. washThe mixture (pH ˜4.0) washed with saturated aqueous NaHCO3 (1×50 mL), water (1×50 mL), and brine (1×50 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-5e949453c23e4b47b986f387ca14d65a
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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