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

HRID 1939160Notes

Reaction equation

HRID 1939160 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 10085361Methyl 2-(N-bromoacetyl-N-methylamino)benzoateYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ba780a7fc7f14b40b789b172ead3450f
Source dataset
uspto-grants-1997_12
Patent number
US05696110

Reaction notes

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