HCID 67312948, compound → HCID 67312934, compound

HRID 1890329Notes

Reaction equation

HRID 1890329 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([N+:24]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.[Zn]>[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH3:23])=[CH:20][CH:21]=2)[C:12]([NH2:24])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67312948HCID 67312948, compound

Product 1

HCID 67312934HCID 67312934, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 6-(benzyloxy)-N-(4-ethylphenyl)-3-nitropyridin-2-amine (987 mg, 2.82 mmol in AcOH (6.0 mL) was added zinc dust (737 mg, 11.2 mmol). The mixture was stirred overnight at room temperature, filtered through Celite®, and concentrated. The crude residue was dissolved in EtOAc and washed with saturated NaHCO3. The organics were dried over MgSO4, filtered, and concentrated to give the title compound as a dark brown oil (716 mg). 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (t, J=7.6 Hz, 3H), 2.62 (q, J=7.6 Hz, 2H), 2.95 (broad s, 2H), 5.32 (s, 2H), 6.20 (d, J=8.1 Hz, 1H), 6.65 (broad s, 1H), 7.05 (d, J=8.1 Hz, 1H), 7.11 (d, J=8.4 Hz, 2H), 7.28-7.41 (m, 8H).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated
  3. dissolutionThe crude residue was dissolved in EtOAc
  4. washwashed with saturated NaHCO3
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3cd5f7c259784f918a417308f530a24f
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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