Methyl N-methylanthranilate → Methyl 2-(N-bromoacetyl-N-methylamino)benzoate

HRID 1939160

Reaktionsgleichung

Reaktionsgleichung von HRID 1939160
[OH-].[Na+].[Br:3][CH2:4][C:5](Br)=[O:6].[CH3:8][NH:9][C:10]1[C:11](=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH3:15])=[O:13]>ClCCl>[Br:3][CH2:4][C:5]([N:9]([C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])[CH3:8])=[O:6]

Komponenten

5

Edukt 3

HCID 6826Methyl N-methylanthranilateHCID 14798Sodium HydroxideHCID 61147Bromoacetyl bromide

Produkt 1

HCID 10085361Methyl 2-(N-bromoacetyl-N-methylamino)benzoateAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sodium hydroxide solution (1.5M, 50 ml) was added dropwise to an ice cooled mixture of bromoacetyl bromide (11 g) and methyl N-methylanthranilate (8.2 g) in dichloromethane (250 ml). After the addition was complete (15 min) stirring was continued at room temperature for 20 min. The organic phase was then separated, washed with 1N HCl (50 ml), brine (50 ml), NaHCO3 solution (50 ml), dried (MgSO4) and evaporated to give a colourless oil which crystallised on standing. Trituration with pet-ether (bp 60°-80°) followed by filtration afforded 10.4 g of product as a colourless solid. 1H NMR (360 MHz, CDCl3) δ: 3.23 (3H, s), 3.54 and 3.60 (2H, ABq J=11 Hz), 3.90 (3H, s), 7.40 (1H, d, J=8 Hz), 7.51 (1H, t, J=8 Hz), 7.65 (1H, t, J=8 Hz), 8.04 (1H, d, J=8 Hz).

Aufarbeitung

  1. temperaturecooled
  2. additionAfter the addition
  3. custom(15 min)
  4. customThe organic phase was then separated
  5. washwashed with 1N HCl (50 ml), brine (50 ml), NaHCO3 solution (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a colourless oil which
  9. customcrystallised
  10. filtrationTrituration with pet-ether (bp 60°-80°) followed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-ba780a7fc7f14b40b789b172ead3450f
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05696110

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