Ammonium Chloride → HCID 26190367, compound

HRID 531439Notes

Reaction equation

HRID 531439 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10])=[C:4]([N+:14]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>[Zn].C1COCC1.O>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10])=[C:4]([CH:3]=1)[NH2:14]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 55136339HCID 55136339, compound

Product 1

HCID 26190367HCID 26190367, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Zinc dust (4.52 g, 69.2 mmol) was added to a stirred solution of 2-(4-bromo-2-nitrophenoxy)-N,N-dimethylethanamine (4 g, 13.8 mmol), ammonium chloride (3.7 g, 69.2 mmol), THF/Water (40/40 mL) at RT. Reaction completed in 4 hours. The RM was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with water, dried over sodium sulfate, concentrated to get the crude mass which was washed with hexanes to afford titled compound 1.85 g (51.67% yield) as solid. 1H NMR (DMSO-d6, 300 MHz): δ 6.74-6.70 (m, 2H), 6.59-6.56 (m, 1H), 4.99 (s, 2H), 3.97-3.93 (t, 2H), 2.59-2.56 (t, 2H), 2.18 (s, 6H). LCMS: m/z=260.8 (M+2).

Workup

  1. customReaction
  2. filtrationThe RM was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto get the crude mass which
  9. washwas washed with hexanes

Sources & evidence

ORD record
ord-aa2ad122788e43f49d49fb4c4e719735
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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