Bromoacetyl bromide → HCID 18929212, compound

HRID 1599818Notes

Reaction equation

HRID 1599818 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:13][CH2:14][C:15](Br)=[O:16]>CN(C=O)C.O1CCOCC1.O>[Br:13][CH2:14][C:15]([NH:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:16]

Participants

6

Reactant 2

HCID 61147Bromoacetyl bromideHCID 2779305-Methoxyanthranilic acid

Product 1

HCID 18929212HCID 18929212, compoundYield 65.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-5-methoxybenzoic acid (5.0 g, 0.03 mol) in anhydrous DMF (30 mL) and dioxane (30 mL) was added, dropwise, bromoacetyl bromide (6.0 g, 2.6 mL, 100 mol %) while keeping the internal temperature between 0° and 2° C. After the addition was completed (~30 min), the reaction mixture was stirred overnight at rt. The reaction mixture was diluted with water (100 mL), and then the precipitated product was filtered, washed sequentially with 5% HBr (300 mL) and water (300 mL), and then dried in a vacuum oven at 40°-45° C., affording 5.6 g (65%) of the title compound as a light grey solid: mp 171.5°-172.7° C.; 1H NMR (DMSO-d6) δ11.26 (s, 1H, NH), 8.30 (d, 1H, J=9.2), 7.44 (d, 1H, J=3.2), 7.22 (dd, 1H, J=3.2, J=9.2), 4.22 (s, 2H), 3.78 (s, 3H); 13C NMR (DMSO-d6) δ168.69, 164.52, 154.75, 133.03, 122.13, 119.83, 119.04, 114.87, 55.40, 30.59; MS (EI, m/z)287 (M+). HRMS (EI) calcd for C10H10NO4Br 286.9793, found 286.9793.

Workup

  1. customthe internal temperature between 0° and 2° C
  2. additionAfter the addition
  3. custom(~30 min)
  4. filtrationthe precipitated product was filtered
  5. washwashed sequentially with 5% HBr (300 mL) and water (300 mL)
  6. customdried in a vacuum oven at 40°-45° C.

Sources & evidence

ORD record
ord-7d0a3a9afe0d4bee98f8fc52c22de2e2
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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