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

HRID 53254

반응식

HRID 53254 반응식
[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>[Br:1][CH2:2][C:3]([N:7]([C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[CH3:6])=[O:4]

참가 물질

6

반응물 3

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

생성물 1

HCID 10085361Methyl 2-(N-bromoacetyl-N-methylamino)benzoate수율 87.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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 (1.41). A solution of sodium hydroxide (59 g) in water (400 ml) was added dropwise and 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 (255 g). 1H NMR (360 MHz, CDCl3) δ3.23 (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, J1 =J2 =8 Hz), 7.65 (1H, dd, J1 =J2 =8 Hz), 8.04 (1H, d, J=8 Hz).

후처리

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

출처 및 근거

ORD 기록
ord-3b0d53543bb343039b0c23b683e56ba3
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618812

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