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

HRID 53254

Reaction equation

HRID 53254 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3b0d53543bb343039b0c23b683e56ba3
Source dataset
uspto-grants-1997_04
Patent number
US05618812

Linked notes

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