Ammonium Chloride → HCID 118098778, compound

HRID 708913Notes

Reaction equation

HRID 708913 reaction equation
[C:1]([CH2:3][C:4]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:5]=1[CH2:6][N:7]([CH3:18])[C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)#[N:2].[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[NH2:23][C:20]1[CH:21]=[CH:22][C:4]([CH2:3][C:1]#[N:2])=[C:5]([CH:19]=1)[CH2:6][N:7]([CH3:18])[C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 118092988HCID 118092988, compound

Product 1

HCID 118098778HCID 118098778, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 36C (1.803 g, 5.31 mmol) in MeOH (30 mL) and THF (10 mL) was added zinc (dust) (3.47 g, 53.1 mmol) and ammonium chloride (5.68 g, 106 mmol). The resulting solution was stirred at rt for 2 h. MeOH was removed under reduced pressure. Na2CO3 (aq, 100 mL) and EtOAc (150 mL) was added, and the suspension was stirred vigorously for 10 min. The mixture was filtered through a glass frit, solid residue was washed with EtOAc (3×150 mL). Combined EtOAc fractions were washed with std. Na2CO3 (aq, 2×50 mL), water (2×50 mL), brine (1×50 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc/hexanes) to give 36D (1.459 g, 4.72 mmol, 89% yield) as a yellowish oil. MS (ESI) m/z: 310.2 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.29-7.46 (5H, m), 7.15 (1H, br. s.), 6.60 (1H, d, J=7.28 Hz), 6.35-6.55 (1H, m), 5.18 (2H, s), 4.44 (2H, s), 3.71 (2H, br. s.), 3.41-3.66 (2H, m), 2.85 (3H, br. s.).

Workup

  1. customMeOH was removed under reduced pressure
  2. additionNa2CO3 (aq, 100 mL) and EtOAc (150 mL) was added
  3. stirringthe suspension was stirred vigorously for 10 min
  4. filtrationThe mixture was filtered through a glass frit, solid residue
  5. washwas washed with EtOAc (3×150 mL)
  6. washCombined EtOAc fractions were washed with std
  7. dry with materialNa2CO3 (aq, 2×50 mL), water (2×50 mL), brine (1×50 mL) and dried (Na2SO4)
  8. customEtOAc was removed under reduced pressure
  9. customthe residue was purified by flash chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-30e8f3ec61f14eb2b123c6c2d55179f5
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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