HCID 59280012, compound → HCID 46205077, compound

HRID 1951318Notes

Reaction equation

HRID 1951318 reaction equation
Cl[CH:2](Cl)[C:3]1[N:4]=[C:5]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=[CH:7][N:6]2[CH:16]=1>C(O)C.CN(C)C1C=CN=CC=1>[CH2:11]([O:12][CH:2]([O:13][CH2:14][CH3:15])[C:3]1[N:4]=[C:5]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=[CH:7][N:6]2[CH:16]=1)[CH3:10]

Participants

4

Reactant 1

HCID 59280012HCID 59280012, compound

Product 1

HCID 46205077HCID 46205077, compoundYield 194.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

To a solution of dichloro compound 2h (1.00 g, 3.66 mmol) in dry ethanol (100 mL), under argon, was added 4-dimethylaminopyridine (DMAP) (0.90 g, 7.38 mmol). The solution was stirred under reflux for 20 h. After cooling to room temperature, the solution was concentrated under vacuo. The resulting precipitate was suspended in ethyl acetate (30 mL), filtered and washed with AcOEt (3×10 mL). The filtrate was evaporated to dryness. The crude product was chromatographed using AcOEt/cyclohexane (8/2, v/v) as eluent to afford compound 2i (1.04 g, 97%). Ketal compound 2i (0.30 g, 4%); mp 98-100° C.; IR (KBr) 1716, 1267, 1166 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.24 (t, 6H, J=7 Hz), 1.41 (t, 3H, J=7 Hz), 3.68 (m, 4H), 4.46 (q, 2H, J=7 Hz), 5.81 (s, 1H), 6.85 (t, 1H, J=7 Hz), 7.78 (s, 1H), 7.90 (d, 1H, J=7 Hz), 8.32 (d, 1H, J=7 Hz); 13C NMR (100 MHz, CDCl3) δ 14.3, 15.3, 61.6, 62.3, 99.0, 111.0, 111.5, 120.2, 128.9, 129.8, 142.0, 146.3, 164.2. MS m/z 293 (M++1, 1), 248 (22), 219 (100), 191 (17), 173 (52), 146 (18) 117 (13).

Workup

  1. temperatureunder reflux for 20 h
  2. concentrationthe solution was concentrated under vacuo
  3. filtrationfiltered
  4. washwashed with AcOEt (3×10 mL)
  5. customThe filtrate was evaporated to dryness
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-c998f5fe0c804f53a41c2a5a8ca10504
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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