Pyridine → HCID 22905634, Verbindung

HRID 1488458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488458
[OH:1][C:2]1[C:3]([CH3:13])=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][CH2:6][CH:5]2[CH3:12].N1C=CC=CC=1.[C:20](Cl)(=[O:24])[CH:21]([CH3:23])[CH3:22]>C(Cl)Cl>[C:20]([N:7]1[C:8]2[C:4](=[C:3]([CH3:13])[C:2]([OH:1])=[C:10]([CH3:11])[CH:9]=2)[CH:5]([CH3:12])[CH2:6]1)(=[O:24])[CH:21]([CH3:23])[CH3:22]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 22905653HCID 22905653, Verbindung

Produkt 1

HCID 22905634HCID 22905634, VerbindungAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To an ice-cold solution of indoline 10 (160 mg, 0.9 mmol) dissolved in methylene chloride (4 mL) and kept under an argon atmosphere were added sequentially pyridine (1 mL) and isobutyryl chloride (0.I mL, 9 mmol); the mixture was stirred over the range of 0° C. to room temperature for some 17 h. The mixture was diluted with methylene chloride, washed with brine and dried (MgSO4). Removal of solvents followed by purification of the residue using 1:9 ethyl acetate:hexanes as eluent afforded the desired N-isobutyryl-5-hydroxy-3,4,6-trimethylindoline (11b, 163 mg, 73% yield) as a colorless solid, mp 123°-125° C. Spectral data: 1H NMR: δ1.1-1.25 (m, 9H), 2.17 (s, 3H), 2.20 (s, 3H), 2.72 (quintet, 1H, J=6.5 Hz), 3.35 (t, 1H, J=6.5 Hz), 3.78 (dd, 1H, J=10.1, 1.0 Hz), 4.13 (t, 1H, J=9.1 Hz), 7.95 (s, 1H); 13C NMR: δ 11.9, 16.5, 18.8, 19.3, 20.7, 33.1, 34.0, 56.3, 116.8, 119.5, 122.1, 134.1, 135.0, 148.8, 175.0; HRMS: calcd. for C15H21NO2 247.1523, fnd. 247.1573. Anal: calcd. for C15H21NO2C, 72.85, H, 8.55, N, 5.66, fnd. C, 72.63, H, 8.59, N, 5.60.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvents
  4. customfollowed by purification of the residue

Quellen und Nachweise

ORD-Eintrag
ord-fc3887e276024ae9bd645069b917c0d0
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674876

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