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

HRID 743697

Reaktionsgleichung

Reaktionsgleichung von HRID 743697
[Br:1][CH2:2][C:3](Br)=[O:4].[CH3:6][NH:7][C:8]1[C:9](=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:10]([O:12][CH3:13])=[O:11].[OH-].[Na+]>ClCCl.O>[CH3:13][O:12][C:10](=[O:11])[C:9]1[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=1[N:7]([C:3](=[O:4])[CH2:2][Br:1])[CH3:6]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 10085361Methyl 2-(N-bromoacetyl-N-methylamino)benzoateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of bromoacetyl bromide (209 g) in dichloromethane (200 ml) was added dropwise to a cooled (ice bath) solution of methyl N-methylanthranilate (168 g) in dichloromethane (1400 ml). A solution of sodium hydroxide (59 g) in water (400 ml) was added dropwise to this ice cold solution then after addition the reaction mixture was stirred at room temperature for 20 h. The organic phase was separated and washed with 1M hydrochloric acid (500 ml), brine (300 ml), saturated sodium hydrogen carbonate solution (400 ml), dried (Na2SO4) then evaporated to afford the required product as a solid (255 g, 92%). Mp 80°-82° C. 1H NMR (360 MHz, CDCl3) δ 3.23 (3H, s), 3.54 (1H, d, J=11 Hz), 3.60 (1H, d, J=11 Hz), 3.90 (3H, s), 7.40 (1H, d, J=8 Hz), 7.51 (1H, dd, J=8 and 8 Hz), 7.65 (1H, dd, J=8 and 8 Hz), 8.04 (1H, d, J=8 Hz).

Aufarbeitung

  1. additionafter addition the reaction mixture
  2. customThe organic phase was separated
  3. washwashed with 1M hydrochloric acid (500 ml), brine (300 ml), saturated sodium hydrogen carbonate solution (400 ml)
  4. dry with materialdried (Na2SO4)
  5. customthen evaporated

Quellen und Nachweise

ORD-Eintrag
ord-eec95826b4f6453a829f8506821d44e8
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556969

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