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

HRID 743697

反応式

HRID 743697 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eec95826b4f6453a829f8506821d44e8
出典データセット
uspto-grants-1996_09
特許番号
US05556969

関連ノート

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