Ammonium Chloride → HCID 59315049, compound

HRID 708840Notes

Reaction equation

HRID 708840 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:3]=1[CH2:4][N:5]([CH3:13])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[Cl-].[NH4+]>C(O)C.[Zn]>[NH2:18][C:15]1[CH:16]=[CH:17][C:2]([Br:1])=[C:3]([CH:14]=1)[CH2:4][N:5]([CH3:13])[C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 59315040HCID 59315040, compound

Product 1

HCID 59315049HCID 59315049, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

Zinc (1.042 g, 15.93 mmol) was added to a mixture of tert-butyl 2-bromo-5-nitrobenzyl(methyl)carbamate (1 g, 2.90 mmol) and ammonium chloride (3.10 g, 57.9 mmol) in ethanol (10 mL). The mixture was stirred for 3 h at rt. The mixture was concentrated. Na2CO3 (sat., 50 mL) and EtOAc (50 mL) was added and stirred for 1 h. The phases were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organics were combined, washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (loading in chloroform, 0% to 50% ethyl acetate in hexane over 30 min using a 40 g silica gel cartridge) to yield 12A (0.785 g, 2.490 mmol, 86% yield) as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. additionNa2CO3 (sat., 50 mL) and EtOAc (50 mL) was added
  3. stirringstirred for 1 h
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (loading in chloroform
  10. wait0% to 50% ethyl acetate in hexane over 30 min using

Sources & evidence

ORD record
ord-56c62c9cbd7d4fde96b98e1b653053be
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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