Acetic Acid → HCID 67224204, Verbindung

HRID 1947647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947647
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH3:28])([CH3:27])[CH2:21][NH:22][C:23]2=[O:26])=[CH:18][CH:17]=1.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.C(O)(=O)C>ClCCl>[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([CH3:28])([CH3:27])[CH2:21][NH:22][C:23]3=[O:26])=[CH:18][CH:17]=2)=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 219596427-Amino-4,4-dimethyl-3,4-dihydroisoquinolin-1(2h)-one

Produkt 1

HCID 67224204HCID 67224204, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (800 mg, 3.79 mmol) was added to a stirred solution of 7-amino-4,4-dimethyl-3,4-dihydro-2H-isoquinolin-1-one (220 mg, 1.15 mmol), 4-chlorobenzaldehyde (324 mg, 2.31 mmol) and acetic acid (69 μl, 1.15 mmol) in anhydrous dichloromethane (10 ml) at room temperature. The reaction was stirred overnight and quenched with the addition of water. The organic phase was separated, washed with brine, then dried (MgSO4) and evaporated in vacuo. The resulting residue was purified by flash column chromatography (20% ethyl acetate in dichloromethane) to afford the title compound as a light brown solid (140 mg, 39%). HPLC retention time 4.40 min. Mass spectrum (ES+) m/z 315 (M+H).

Aufarbeitung

  1. customquenched with the addition of water
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe resulting residue was purified by flash column chromatography (20% ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-add29f979b4b4f1abadcb8bd616fec3a
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399481B2

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