Ethyl chloroacetate → 6-Bromo-2-oxo-benz[cd]indole-1(2H)-acetic Acid, Ethyl Ester

HRID 1164320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1164320
[H-].[Na+].[Br:3][C:4]1[C:5]2[C:6]3[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]=3[CH:14]=[CH:15][CH:16]=2.[H][H].[H-].Cl[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[Br:3][C:4]1[C:5]2[C:6]3[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:8](=[O:13])[C:7]=3[CH:14]=[CH:15][CH:16]=2

Komponenten

7

Edukt 5

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 166653HydrideHCID 7547635-Bromo-8-naphtholactamHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 130842616-Bromo-2-oxo-benz[cd]indole-1(2H)-acetic Acid, Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (0.63 g, 0.0262 mol; 1.26 g of a 50% mineral oil suspension) was added portionwise with stirring to a solution of 6-bromo-benz[cd]indol-2(1H)-one (6.5 g, 0.0262 mol) in dry dimethylformamide (20 mL) allowing hydrogen evolution to cease before adding the next portion of hydride. To the cooled (ice-bath), stirred solution was added ethyl chloroacetate (3.53 g, 3.17 mL, 0.0288 mol) and the mixture was refluxed for 3 hr. The solvent was evaporated in vacuo and the residue was triturated with water (the mixture was stirred overnight at room temperature). The precipitate was separated by filtration, washed with water and hexane (10 mL; to remove mineral oil), dried (8.4 g) and crystallized from ethanol to give the title compound (5.8 in two crops): mp 128°-130° C.; Anal. Calcd for C15H12BrNO3 : C, 53.91% H, 3.62% N, 4.19%; Found: C, 53.58% H, 3.75% N, 4.26%; IR (CHCl3) 1744, 1708, 1629, 1602, and 1194 cm-1 ; UV max (methanol) 339 (ε5600), 323 (2800), 289 (sH, 4650), 279 (6200), and 258 nm (18,600);, and NMR (CDCl3)δ 1.25 (t, 3H), 4.20 (q, 2H), 4.62 (s, 2H), 6.63 (d, 1H), 7.60 (d, 1H), 7.77 (d, 1H), 8.07 (m, 2H).

Aufarbeitung

  1. addition1.26 g of a 50% mineral oil suspension) was added portionwise
  2. temperatureTo the cooled (ice-bath)
  3. temperaturethe mixture was refluxed for 3 hr
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was triturated with water (the mixture
  6. stirringwas stirred overnight at room temperature)
  7. customThe precipitate was separated by filtration
  8. washwashed with water and hexane (10 mL; to remove mineral oil)
  9. customdried (8.4 g)
  10. customcrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b7236cc1f553472089b6d97a8e3b5f08
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04369188

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