Benzyl Alcohol → HCID 67312948, compound

HRID 1890328Notes

Reaction equation

HRID 1890328 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[N:17]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=2)[C:15]([N+:27]([O-:29])=[O:28])=[CH:14][CH:13]=1>C1COCC1>[CH2:1]([O:8][C:12]1[N:17]=[C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH3:26])=[CH:23][CH:24]=2)[C:15]([N+:27]([O-:29])=[O:28])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 43330298HCID 43330298, compound

Product 1

HCID 67312948HCID 67312948, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of benzyl alcohol (1.32 g, 12.2 mmol) in THF (15 mL) at room temperature was added sodium hydride (60% dispersion in mineral oil, 488 mg, 12.2 mmol). The mixture was stirred at room temperature for 0.5 h at which time 6-chloro-N-(4-ethylphenyl)-3-nitropyridin-2-amine (1.21 g, 4.03 mmol) was added. The mixture was heated in a sealed tube overnight at 65° C. The reaction vessel was cooled to room temperature and the mixture was quenched with saturated NaHCO3. The mixture was extracted with EtOAc and the organics were dried over MgSO4, filtered, and concentrated. Purification by silica gel chromatography (2% EtOAc in hexanes gradient to 15% EtOAc in hexanes) gave the title compound (987 mg) as a yellow solid. NMR (400 MHz, CDCl3) δ ppm 1.26 (t, J=7.6 Hz, 3H), 2.66 (q, J=7.6 Hz, 2H), 5.34 (s, 2H), 6.25 (d, J=9.1 Hz, 1H), 7.20 (d, J=8.4 Hz, 2H), 7.41-7.28 (m, 5H), 7.45 (d, J=8.4 Hz, 2H), 8.40 (d, J=9.1 Hz, 1H), 10.51 (broad s, 1H).

Workup

  1. additionwas added
  2. temperatureThe reaction vessel was cooled to room temperature
  3. customthe mixture was quenched with saturated NaHCO3
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (2% EtOAc in hexanes gradient to 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d4daa95ebb4e4f8b918c35e582a88f04
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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