Sodium Carbonate → 4'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde oxime

HRID 989270

Reaktionsgleichung

Reaktionsgleichung von HRID 989270
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:28][OH:29]>C(O)C>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]=[N:28][OH:29])=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 98139384'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde

Produkt 1

HCID 734155234'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde oximeAusbeute 33,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of Example 27 (33.7 mg), sodium carbonate (27.6 mg), and hydroxylamine hydrochloride (18 mg) in ethanol (5 mL) was set to reflux for 16 hours. Inorganic solid was filtered out and washed with DCM and acetone. Organic layer was concentrated under reduced pressure to give the titled compound (12 mg) without purification. 1H NMR (400 MHz, CDCI3)δ8.19 (s, 1 H), 7.82-7.69 (m, 8 H), 4.37 (d, J=6.3, 2 H), 3.35 (m, 2 H), 3.10-3.03 (m, 2 H), 2.06-1.94 (m, 2 H), 1.93-1.88 (m, 2 H).

Aufarbeitung

  1. temperatureto reflux for 16 hours
  2. filtrationInorganic solid was filtered out
  3. washwashed with DCM and acetone
  4. concentrationOrganic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-13ed004ddf744982968e36e7e5a8dc90
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638967B2

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